Vilsmeier-Haack Synthesis of 2,5-dimethyl-1H-(p-tolyl)-pyrrole-3-carboxaldehyde

Vilsmeier-Haack Synthesis of 2,5-dimethyl-1H-(p-tolyl)-pyrrole-3-carboxaldehyde



DMF (1.5 mL, 19.4 mmol, 6.5 equiv.) was stirred under a nitrogen atmosphere in an ice-bath. Phosphoryl chloride (0.308 mL, 3.3 mmol, 1.1 equiv.) was added and the reaction stirred for 30 minutes. Reaction mixture was a very pale yellow. A solution of 2,5-dimethyl-1H-(p-tolyl)-pyrrole (556 mg, 3 mmols, 1 equiv.) in DMF (2 mL) was added dropwise over 1 minute. After 5 minutes, flask removed from ice and reaction stirred for a further 55 mins. TLC at 1 hr showed reaction at completion. Reaction mixture was then poured onto ice (50 mL) and 1M NaOH added (pH 11), until adjusted to pH 6. Total volume approximately 50 mL after ice has melted and solution was pH 3 the next day. 20% NaOH was added to achieve pH 11 and flask bathed in a brine ice-bath for 20 minutes. Product filtered and washed with water to produce a wet brown paste. Product was dissolved in MeCN and concentrated under a nitrogen atmosphere. Brown solution with precipitation of fine crystals was observed overnight. Solution was cooled in an ice bath and filtered. Filter cake washed with water (3 x 10 mL). Filtered product was then dried under vacuum to produce a lumpy grey-brown powder (423 mg, 71%).

Collected data: 2,5-dimethyl-1H-(p-tolyl)-pyrrole-3-carboxaldehyde

mpt: 109-111^oC
¹H-NMR (300 MHz, CDCl₃): δ 9.86 (s, 1H), 7.30, 7.33 (d, 2H), 7.06, 7.09 (d, 2H), 6.37 (s, 1H), 2.44 (s, 3H), 2.27 (s, 3H), 1.98 (s, 3H)
¹³C-NMR (75 MHz, CDCl₃): δ 185.18, 138.98, 138.94, 134.30, 131.08, 130.18, 127.65, 121.82, 105.63, 21.19, 12.64, 11.19 
m/z (ESI+/-): 214 [M+H]⁺, 100% 
IR: 810.51, 1421.53, 1514.85, 1651.24, ~3934.95


References:
doi: 10.1002/cmdc.200600026

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Ethyl 2,5-dimethyl-1-[p-(trifluoromethyl)phenyl]-1H-pyrrole-3-carboxylate

Ethyl 2,5-dimethyl-1-[p-(trifluoromethyl)phenyl]-1H-pyrrole-3-carboxylate 


HAS A TRIFLUORO GP


Synthesis of ethyl 2,5-dimethyl-1-[p-(trifluoromethyl)phenyl]-1H-pyrrole-3-carboxylate from condensation of p-(trifluoromethyl)aniline with ethyl 2-acetyl-4-oxopentanoate.



Ethyl acetoacetate (6 mL,47 mmol, 1 equiv.) and K₂CO₃ (8.45 g, 61.1 mmol, 1.3 equiv.) were mixed in MeCN (55 mL). NaI (7.05 g, 47 mmol, 1 equiv.) and Chloroacetone (4.8 mL, 51.7 mmol, 1.1 equiv.) were added and mixture heated to 80^oC in an oil bath. TLC at 2 hours showed reaction at completion. Reaction was allowed to cool to room temperature. Mixture washed with EtOAc (2 x 20 mL), water (2 x 20 mL), 1:1 water:brine (2 x 20 mL) and brine (2 x 20 mL) and dried with MgSO4 and concentrated under reduced pressure to form a yellow oil.

Ethyl 2-acetyl-4-oxopentanoate intermediate  (2 mL, 10.7 mmol, 1 equiv.) was added to p-(trifluoromethyl)aniline (1.62 mL, 12.9 mmol, 1.2 equiv.) and heated at 80^oC in an oil bath for 1.25 hrs. TLC at 1 hour showed reaction at completion and reaction was allowed to cool to room temperature. Product was washed with EtOAc (2 x 20 mL), 10% citric acid (3 x 20 mL), water (20 mL) and brine (2 x 20 mL) and then concentrated under reduced pressure to form a dark brown oil. Brown oil was dissolved in 20 mL EtOH and heated before filtering under heat to remove residual salts and washing with hot EtOH. Filtrate was concentrated under reduced pressure and purified by chromatography on silica (2-15% EtOAc in petrol). Pure fractions were taken and concentrated under reduced pressure to produce a light yellow oil. Product was cooled in a refrigerator overnight forming a pale yellow crystalline solid (1.85 g, 55%).


data: ethyl 2,5-dimethyl-1-[p-(trifluoromethyl)phenyl]-1H-pyrrole-3-carboxylate 

mpt: 66-68^oC

m/z (APCI+): 312[M+H]⁺, 100%


¹H-NMR (300 MHz, CDCl₃): 
δ 7.77, 7.80 (d, 1H), 7.32, 7.35 (d, 1H),6.41 (s, 1H), 4.25-4.32 (qr, 2H), 

2.30 (s, 3H), Methyls on pyrrole ring
1.99 (s, 3H), Methyls on pyrrole ring
1.33-1.37 (t, 3H)  CH2CH3


¹³C-NMR (75 MHz, CDCl₃): δ 165.5 140.98, 135.85, 131.00, 128.76, 128.47, 126.64, 126.59, 125.50, 121.89, 112.24, 108.24, 59.38, 14.52, 12.65, 12.35


¹⁹F-NMR (280 MHz, CDCl₃): δ -62.65


IR: 770.27, 840.98, 1065.03, 119.55, 1215.36, 1322.48, 1413.83, 1613.74, 1681.96, 2928.23


NMR Spectra:

1H NMR.........http://malaria.ourexperiment.org/data/704.html

13C NMR..........http://malaria.ourexperiment.org/data/706.html

19F NMR........http://malaria.ourexperiment.org/data/708.html

WITHOUT THE FLUORO GP

Synthesis of ethyl 2,5-dimethyl-1-phenyl-1H-pyrrole-3-carboxylate from condensation of aniline with ethyl 2-acetyl-4-oxopentanoate 


Ethyl acetoacetate (6 mL,47 mmol, 1 equiv.) and K₂CO₃ (8.45 g, 61.1 mmol, 1.3 equiv.) were mixed in MeCN (55 mL). NaI (7.05 g, 47 mmol, 1 equiv.) and Chloroacetone (4.8 mL, 51.7 mmol, 1.1 equiv.) were added and mixture heated to 80^oC in an oil bath. TLC at 2 hours showed reaction at completion. Reaction was allowed to cool to room temperature. Mixture washed with EtOAc (2 x 20 mL), water (2 x 20 mL), 1:1 water:brine (2 x 20 mL) and brine (2 x 20 mL) and dried with MgSO4 and concentrated under reduced pressure to form a yellow oil. Ethyl 2-acetyl-4-oxopentanoate intermediate (2 mL, 10.7 mmol, 1 equiv.) was added to Aniline (1.17 mL, 12.89 mmol, 1.2 equiv.) and heated at 80^oC in an oil bath for 1.25 hrs. TLC at 1 hour showed reaction at completion and reaction was allowed to cool to room temperature. Product was washed with EtOAc (2 x 20 mL), 10% citric acid (3 x 20 mL), water (20 mL) and brine (2 x 20 mL) and then concentrated under reduced pressure to form a dark brown oil. Product was purified by chromatography on silica (2-15% EtOAc in petrol – suggest a lower % EtOAc). Product containing fractions concentrated under reduce pressure to produce a yellow oil (952 mg, approximate yield 37%). Product did not crystallise.

data: ethyl 2,5-dimethyl-1-phenyl-1H-pyrrole-3-carboxylate

mpt: n/a
m/z (APCI+): 244 [M+H]⁺, 100%
¹H-NMR (300 MHz, CDCl₃): δ 7.41-7.50 (qn, 2H), 7.15, 7.18 (m, 2H), 6.38 (s, 1H), 4.20-4.32 (sx, 2H), 2.29 (s, 3H), 1.97 (s, 3H), 1.27-1.36 (qn, 3H)
¹³C-NMR (75 MHz, CDCl₃): δ 165.72, 137.76, 136.16, 129.39, 129.19, 128.93, 128.68, 128.53, 128.18, 111.49, 107.55, 59.21, 14.59, 12.64, 12.37
IR: 696.57, 770.6, 1072.8, 121.34, 1411.26, 1693.25, 2978.29

NOW WITH A METHYL

ethyl 2,5-dimethyl-1-(p-tolyl)-1H-pyrrole-3-carboxylate from condensation of p-toluidine with ethyl 2-acetyl-4-oxopentanoate.


Ethyl acetoacetate (2 mL, 15.7mmol, 1 equiv.) and K₂CO₃ (2.82 g, 20.4 mmol, 1.3 equiv.) in MeCN (30 mL) were mixed. Chloroacetone (1.6 mL, 17.2 mmol, 1.1 equiv.) and NaI (2.7 g, 18 mmol, 1.15 equiv.) were added and heated in an oil bath at 80°C. TLC showed reaction at completion after 2.5 hrs. After 3 hrs reflux, solution was allowed to cool to room temperature and then filtered and washed with EtOAc (30 mL). Mixture was concentrated under reduced pressure, dissolved in EtOAc (40 mL) and washed with water (20 mL), 1:1 water:brine (20 mL) and brine (20 mL). Crude product was then concentrated under reduced pressure. p-toluidine (2.02 g, 18.8 mmol, 1.2 equiv.) was added to crude intermediate and heated in an oil bath at 90°C. At 1.5 hrs, reaction was complete by TLC and reaction was allowed to cool to room temperature. Dark brown product was washed with EtOAc (2 x 20 mL), 10% citric acid (3 x 20 mL), water (2 x 20 mL) and brine (20 mL) and then concentrated under reduced pressure to form a black oil. Product was dissolved in EtOH and activated charcoal added to remove coloured impurities. Product was stirred for 1 hr then filtered and washed with EtOH. Filtrate was concentrated under reduced pressure to form a black oil. Oil was purified by chromatography on silica (2-10% EtOAc in petrol). Pure and impure fractions were taken separately and concentrated under reduced pressure to produce yellow and dark yellow oils respectively. Pure fraction crystallised overnight to a bright yellow crystalline solid (1.8 g, 45.6%).

Collected data: ethyl 2,5-dimethyl-1-(p-tolyl)-1H-pyrrole-3-carboxylate

mpt: 60-63^oC
m/z (APCI+): 258 [M+H]⁺, 100%
¹H-NMR (300 MHz, CDCl₃): δ 7.29, 7.26 (d, 2H), 7.03, 7.06 (d, 2H), 6.36 (s, 1H), 4.24-4.31 (qr, 2H), 2.42 (s, 3H), 2.28 (s, 3H), 1.96 (s, 3H), 1.32-1.36 (t, 3H) 
¹³C-NMR (75 MHz, CDCl₃): δ 165.75, 138.46, 136.28, 135.12, 129.99, 128.78, 127.88, 111.31, 107.36, 59.17, 21.15, 14.59, 12.63, 12.36 
IR: 767.43, 1080.99, 1218.07, 1411.09, 1515.22, 1693.11, 2982.09

LUCITANIB

LUCITANIB

6-[7-[(1-aminocyclopropyl)methoxy]-6-methoxyquinolin-4-yl]oxy-N-methylnaphthalene-1-carboxamide

6-(7-((l-aminocyclopropyl)methoxy)-6-methoxyquinolin-4-yloxy)- N-methyl- 1 -naphthamide

1058137-23-7 (E-3810 free base); 1058137-84-0  (E-3810 HCl salt)

E-3810, E-3810 amine, UNII-PP449XA4BH, E3810, Lucitanib [INN], AL3810

Molecular Formula:C26H25N3O4

Molecular Weight:443.4944 g/mol

Advenchen Pharmaceuticals, LLC

SYN..........http://newdrugapprovals.org/2015/01/28/lucitanib-a-vegfrfgfr-dual-kinase-inhibitor-in-phase-2-triald/

http://www.google.com/patents/WO2010105761A1?cl=en

Example 7: Preparation of 6-(7-((l-aminocyclopropyl)methoxy)-6- methoxyquinolin-4-yloxy)-N-methyl-l-naphthamide (I)

A mixture of the compound of Example 6 (0.24 g, 0.42 mmol) in 2 ml of a solution of 40% HBr in acetic acid was stirred at 300C for 3h, then added with 10 ml of water and the reaction mixture was extracted with AcOEt (2 x 10 mL). The organic phases were removed. The aqueous solution was dropwise added with a solution of 50% NaOH to reach pH 10. The mixture was extracted with DCM (3 x 20 mL) and the combined organic phases were dried and evaporated to give a crude containing 6-(7-((l-aminocyclopropyl)methoxy)-6-methoxyquinolin-4- yloxy)-N-methyl-l-naphthamide (I) with purity higher than >94% by LC-MS analysis. This crude was further purified by chromatography on a silica gel column eluting with DCM/MeOH 10: 1), to afford 6-(7-((l- aminocyclopropyl)methoxy)-6-methoxyquinolin-4-yloxy)-N-methyl-l- naphthamide (I) having purity higher than 98% by LC-MS analysis (140 mg, yield: 76%).

1H-NMR (500 MHz, DMSO-d6) δ ppm: 8.47 (d, 2 H), 7.87 (d, 1 H), 7.53 (m, 3 H), 7.51 (m, 1 H), 7.44 (d, 1 H), 7.38 (s, 1 H), 6.50 (d, 1 H), 6.16 (d, 1 H), 5.01 (s, 2 H), 4.05 (s, 2 H), 4.03 (s, 3 H), 3.12 (d, 3 H), 2.09 (m, 2 H), 0.80 (m, 4 H).

LC-MS: M+H+: 444.0

SYN..........http://newdrugapprovals.org/2015/01/28/lucitanib-a-vegfrfgfr-dual-kinase-inhibitor-in-phase-2-triald/

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(+)-Sitophilure

(+)-sitophilure

IUPAC Name: (4S,5R)-5-hydroxy-4-methylheptan-3-one | CAS Registry Number: 71699-35-9
Synonyms: Sitophilure, CID155663, 3-Heptanone, 5-hydroxy-4-methyl-, (R*,S*)-, 71699-35-9 

(+)-(4S,5R)-5-Hydroxy-4-methyl-3-pentanone (1)

To a solution of oxalyl chloride (0.013 mL, 0.15 mmol) in CH₂Cl₂ (1.0 mL) at -78 °C was added dimethyl sulfoxide (0.020 mL, 0.31 mmol) dropwise. The solution was stirred 10 min at -78 °C and a solution of a mixture of 11 and 12 (0.023 g, 0.089 mmol) in CH₂Cl₂ (1.0 mL) was added. The mixture was stirred 1.5 h at -78 °C, and treated with triethylamine (0.06 mL, 0.46 mmol). After warming to room temperature, the reaction was quenched with water, the layers were separated and the aqueous layer was extracted with CH₂Cl₂ (3 x 2 mL). The combined organic phases were washed with brine (4 mL), dried over MgSO₄ and concentrated under reduced pressure. The residue (0.019 g) was dissolved in THF (1 mL) at room temperature and treated with 1.0 M solution of TBAF (0.1 mL, 0.1 mmol) in THF. The mixture was stirred 1 day at room temperature, diluted with Et₂O (10 mL) and treated with aq. NH₄Cl (3 mL). The layers were separated and the aqueous layer was extracted with Et₂O (3 x 4 mL). The combined organic layers were dried over MgSO₄ and concentrated. Silica gel chromatography (30% AcOEt in hexanes, v/v) afforded (+)-1 (0.0074 g, 0.052 mmol) in 60% yield, as a colorless oil.

 ¹H-NMR (CDCl₃, 300 MHz): d 0.96 (t, 3H, J = 7 Hz); 1.06 (t, 3H, J = 7 Hz); 1.14 (d, 3H, J = 7 Hz); 1.37 (ddq, 1H, J = 15, 7 and 3 Hz); 1.51 (ddq, 1H, J = 15, 8 and 7 Hz); 2.42-2.70 (m, 3H); 2.86 (br s, 1H); 3.83 (ddd, 1H, J = 8, 5 and 3 Hz). 

¹³C-NMR (CDCl₃, 75.5 MHz): d 7.6; 9.9; 10.4; 26.8; 35.1; 49.3; 72.6; 216.8.

 IR (film): 3453; 1701; 1460 cm^-1. [a]_D +24.8 (c1.24, Et₂O). lit.²: [a]_D +27.0 (c1.24, Et₂O).

J. Braz. Chem. Soc. vol.10 no.5 São Paulo Sept./Oct. 1999

http://dx.doi.org/10.1590/S0103-50531999000500005 

Article

The Asymmetric Synthesis of (+)-Sitophilure, the Natural Form of the Aggregation Pheromone of Sitophilus oryzae L. and Sitophilus zeamais M.

Ronaldo A. Pilli*, and Valéria B. Riatto

Instituto de Química, UNICAMP, C.P. 6154, 13083-970 Campinas - SP Brazil

http://www.scielo.br/scielo.php?pid=S0103-50531999000500005&script=sci_arttext

*e-mail: pilli@iqm.unicamp.br  and vbriatto@iqm.unicamp.br

Ronaldo Aloise Pilli


http://www.google.com/patents/US20090298147............


In 1984, Burkholder and coworkers isolated the male-produced aggregation pheromone of the pests rice weevil (Sitophilus oryzae L.) and maize weevil (Sitophilus zeamais M.), which is named Sitophilure.^[8] This biologically-active compound was first identified as (4R,5S)-5-hydroxy-4-methyl-3-heptanone, from the extracts of thousands of insects. All four stereoisomers of this pheromone were synthesized and it was proved that the active form of this compound is the (4S,5R) enantiomer.^[9] Since then, several total syntheses of racemic,^[10] or other stereoisomers^[11] and the natural form^[12] of this pheromone have been published.
Serious economic losses of stored cereal grains (maize, rice and grain) are mainly caused by three weevils of the genus Sitophilus (Sitophilus zeamais, Sitophilus oryzae, Sitophilus granarius respectively) throughout the world. Early detection of infestations is critical in order to avoid further damage to the grains and the subsequent economic losses. Traps that contain very small amounts of synthetic (+)-sitophilure have been shown to be very effective in the early detection of all three species of weevils,^[13] however a simple scalable and economic method for the synthesis of this weevil attractant pheromone is still lacking.^[9-12] As a result, all of the commercially available traps for the early detection of these weevils are food-based.


The absolute stereochemistry of the enantiomers B and D (Scheme 3) was found to be (4S,5R) and (4S,5S) respectively, taking into account that the relative stereochemistry of the product D is anti and of the product B syn.

As we can see in Scheme 3, the product from the reduction of 4-methyl-3,5-heptanedione with KRED-A1C has the same stereochemistry with that of the natural pheromone (+)-Sitophilure. These results clearly indicate that ketoreductases KRED-A1B, KRED-A1C and KRED-A1D showed unusual anti-Prelog selectivity, concerning reduction of the 5-keto group and successfully produced the keto alcohol with the desired stereochemistry 4S,5R. So the natural product can be produced easily from the corresponding diketone.
In large scale, the reaction is completed in 24 hours, producing the pheromone with chemical yield 85%, de 96%, ee >99%, and chemical purity >99%, utilizing catalytic amounts of the NADPH cofactor (0.81% relative to the substrate), which was recycled in situ using Glucose Dehydrogenase (GDH). The corresponding 4-methyl-3,5-heptanedione can be readily produced from the commercially available 3,5-heptanedione (Scheme 4).

Synthesis of (4S,5R)-5-hydroxy-4-methyl-3-heptanone
A phosphate-buffered solution (16 mL, pH 6.5, 200 mM) containing 84 mM (1.35 mmol, 192 mg) of 4-methyl-3,5-heptanedione, NaCl (200 mM, 200 mg), glucose (130 mM, 375 mg), NADPH (0.69 mM, 0.011 mmol, 10 mg), glucose dehydrogenase (10 mg) and KRED-A1C (10 mg) was stirred at 25° C. for 24 hours, until GC analysis of crude extracts showed complete reaction. Periodically the pH was readjusted to 6.5 with NaOH (2 M). The product was isolated by extracting the crude reaction mixture with EtOAc (15 mL×2). The combined organic layers were then extracted with saturated NaCl solution, dried over MgSO₄ and evaporated to dryness. Pure (4S,5R)-5-hydroxy-4-methyl-3-heptanone (165 mg) was obtained in 85% yield. ¹H NMR (CDCl₃ 500 MHz, δ ppm): ¹H NMR (CDCl₃ 500 MHz, δ ppm): 3.77-3.85 (m, 1H), 2.72 (s, OH), 2.41-2.64 (m, 3H), 1.32-1.58 (m, 2H), 1.12 (d, J=7.1 Hz, 3H), 1.05 (t, J=7.3 Hz, 3H), 0.95 (t, J=7.4 Hz, 3H). ¹³C NMR (CDCl₃ 300 MHz, δ ppm): 216.7, 72.6, 49.3, 35.1, 26.9, 10.4, 9.9, 7.6.
Determination of the Enantiomeric Purity of (4S,5R)-5-hydroxy-4-methyl-3-heptanone: GC (column: 30 m×0.25 mm×0.25 μm chiral capillary column, 20% permethylated cyclodextrin 65° C. for 100 min, rate: 1° C./min, final temp.: 100° C.; carrier gas: N₂, press 70 kPa). t_R=100.0 min [98%, (4S,5R)-5-hydroxy-4-methyl-3-heptanone], t_R=105.1 min [2%, (4R,5R)-5-hydroxy-4-methyl-3-heptanone]. The enantiomeric purity was estimated to be >99% and the diastereomeric purity 96%.

 

Administração e Biblioteca do Instituto de Química da UNICAMP, Campinas.

Instituto de Química - Unicamp

Lab. de Ensino, Biblioteca e Administração

Campinas
Municipality
The Municipality of Campinas
Images from top, left to right: Metropolitan Cathedral, an avenue in Campinas's downtown, an old railway station, Mogiana Palace, a monument to the heroes of Constitutionalist Revolution (in Saudade Cemetery), a bus terminus, Central area of Campinas as seen from Torre do Castelo, a belvedere.
Flag Seal
Nickname(s): Cidade das Andorinhas, Brazilian Silicon Valley, Princesa d'Oeste
Location of Campinas
Campinas Location in Brazil
Coordinates: 22°54′3″S 47°03′26″W
Country	Brazil
Region	Southeast
State	São Paulo
Founded	July 14, 1774
Government
• Mayor	Jonas Donizette (PSB)
Area
• Municipality	795.667 km2 (307.209 sq mi)
• Metro	3,645 km2 (1,407 sq mi)
Elevation	555-780 m (1,821–2,559 ft)
Population (2012)
• Municipality	1,098,630 (14th)
• Density	1,358.6/km2 (3,519/sq mi)
• Metro	2,633,523
Time zone	Brasilia Official Time (UTC-3)
• Summer (DST)	Brazilian Daylight Saving Time (UTC-2)
Postal Code	13000-000
Area code(s)	+55 19
Website	Campinas, São Paulo

History

Campinas in 1878

Maps of railways in Campinas in 1929

Regatas Club in Cambuí neighborhood.

   Instituto de Química

1. • 
2. 

 

 

Formação Acadêmica

MS-6, Professor Titular; Bel. Instituto de Quimica, UNICAMP (1976), Dr. Sc. (UNICAMP, 1982); Pós-doutorado (University of California, Berkeley,1982-84); Professor Titular (UNICAMP, 2002)

Contato

Instituto de Química
Caixa Postal 6154
Campinas, SP
13083-862 Sala D-353
Fax 55 19 3521 3023
Fone 55 19 3521-3422
pilli@iqm.unicamp.br
Currículo Lattes

Pesquisa

- Síntese Orgânica
- Síntese de Produtos Naturais
- Síntese Assimétrica de Fármacos
- Estudos de Estrutura x Atividade Biológica

Publicação

1. PILLI, R. A. ; Ângelo de Fátima ; Luciana Konecny Kohn ; CARVALHO, J. E. . Cytotoxic Activity of (S)-goniothalamin and Analogues Against Human Cancer Cells. Bioorganic & Medicinal Chemistry, Estados Unidos, v. 14, p. 622-631, 2006.
2. PILLI, R. A. ; Andrea Leal de Sousa . A concise route to the azaspirodecane moiety of halichlorine and structurally related alkaloids. Organic Letters, Washington, DC, v. 7, p. 1617-1619, 2005.
3. PILLI, R. A. ; MALDANER, A. O. ; CORREA JR., I. R. ; ROSSO, G. B. . Total Synthesis and Structural Elucidation of Natural Products: (-)-Delactonmycin, (+)-Plumerinine and (-)-Parvistemoamide . Pure and Applied Chemistry, Grã-Bretanha, v. 77, p. 1153-1160, 2005.
4. PILLI, R. A. ; SANTOS, L. S. ; RAWAL, V. . Enantioselective Total Syntheses of (+)-Arborescidine A, (-)-Arborescidine B, and (-)-Arborescidine C. Journal of Organic Chemistry, Washington, DC, v. 69, p. 1283-1288, 2004.
5. PILLI, R. A. ; CORREA JR., I. R. . Total Synthesis and Structural Elucidation of (-)-Delactonmycin. Angewandte Chemie, Alemanha, v. 42, p. 3017-3020, 2003.

  
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