COSY Spectrum of m-dinitrobenzene

COSY Spectrum of m-dinitrobenzene




 

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New Furanones from the Plant Endophytic Fungus Pestalotiopsis besseyi

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 Structures of compounds 1–5.

The fermented material was freeze-dried and extracted with methyl ethyl ketone (3 × 500 mL), and the organic solvent was evaporated to dryness under vacuum to afford 5.0 g of crude extract. The extract was fractionated by silica gel column chromatography (5 × 40 cm) using CHCl₃–CH₃OH gradient elution. The fraction (50 mg) that was eluted with 1% MeOH was further separated by semipreparative reversed-phase HPLC (Kramosil C₁₈ column; 10-µm; 10 × 250 mm, 2 mL/min) to afford pestalafuranone B (2; 1.9 mg, t_R 15.3 min; 50% MeOH in H₂O over 2 min, 50–72% over 10 min, 72–74% over 13 min). The fraction (180 mg) that was eluted with 2% MeOH was then separated by Sephadex LH-20 column chromatography (CH₂Cl₂–n-C₆H₁₄ = 4:1) to afford six fractions. Fraction 3 (60 mg) was successively separated by semipreparative reversed-phase HPLC (32% MeOH in H₂O over 2 min, 32–55% over 60 min) afforded pestalafuranones A (1; 1.6 mg, t_R 25.7 min), C (3; 6.0 mg, t_R 26.6 min), D (4; 1.5 mg, t_R 30.0 min), and E (5; 3.5 mg, t_R 31.5 min).
Pestalafuranone A (1): colorless oil; UV (CH₃OH) λ_max 272 (ε 7800), 265 (ε 6600) nm; IR (Neat) ν_max 2962, 1748, 1717, 1448, 1364 cm⁻¹; ¹H- and ¹³C-NMR data, see Table 1 and Table 2; HRESIMS obsd. m/z 217.0840 [M+Na]⁺ (calcd for C₁₁H₁₄O₃Na, 217.0835).
Pestalafuranone B (2): pale yellow oil; [α]_D −16 (c 0.05, CH₃OH); UV (CH₃OH) λ_max 270 (ε 3300) nm; IR (Neat) ν_max 3403 (br), 2932, 1749, 1446 cm⁻¹; ¹H- and ¹³C-NMR data, see Table 1 and Table 2; HRESIMS obsd. m/z 217.0842 [M+Na]⁺ (calcd for C₁₁H₁₄O₃Na, 217.0835).
Pestalafuranone C (3): pale yellow oil; UV (CH₃OH) λ_max 265 (ε 6600), 235 (ε 4300) nm; IR (Neat) ν_max 2919, 1752, 1717, 1445, 1365 cm⁻¹; ¹H- and ¹³C-NMR data, see Table 1 and Table 2; HRESIMS obsd. m/z 219.0998 [M+Na]⁺ (calcd for C₁₁H₁₆O₃Na, 219.0992).
Pestalafuranone D (4): colorless oil; [α]_D +32 (c 0.05, CH₃OH); UV (CH₃OH) λ_max 275 (ε 4460) nm; IR (Neat) ν_max 2963, 1751, 1450, 1381 cm⁻¹; ¹H- and ¹³C-NMR data, see Table 1 and Table 2; HRESIMS obsd. m/z 217.0846 [M+Na]⁺ (calcd for C₁₁H₁₄O₃Na, 217.0835).
Pestalafuranone D (5): colorless oil; [α]_D +16 (c 0.05, CH₃OH); UV (CH₃OH) λ_max 275 (ε 6270) nm; IR (Neat) ν_max 2931, 1753, 1446, 1346 cm⁻¹; ¹H- and ¹³C-NMR data, see Table 1 and Table 2; HRESIMS obsd. m/z 219.0995 [M+Na]⁺ (calcd for C₁₁H₁₆O₃Na, 219.0992).

Molecules 2012, 17(12), 14015-14021; doi:10.3390/molecules171214015

 New Furanones from the Plant Endophytic Fungus Pestalotiopsis besseyi
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EXAMPLES OF COSY NMR

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2D NMR PRESENTATION BY DR ANTHONY CRASTO

2D NMR PRESENTATION BY DR ANTHONY CRASTO

2D NMR ORGANIC SPECTROSCOPY by DR ANTHONY CRASTO from Anthony Melvin Crasto Ph.D






 

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2-phenyl-1,3-dioxep-5-ene

 

Name:

1,3-Dioxepin,4,7-dihydro-2-phenyl-

Molecular Formula:

C₁₁H₁₂O₂

CAS Registry Number:

2568-24-3

Synonyms:

2-Phenyl-1,3-dioxacyclohept-5-ene; 2-Phenyl-1,3-dioxep-5-ene; 4,7-Dihydro-2-phenyl-1,3-dioxepin;

    2-phenyl-1,3-dioxep-5-ene .            

 


The first enantioselective synthesis of (−)-conolutinine was achieved in 10 steps. The synthesis featured a catalytic asymmetric bromocyclization of tryptamine to forge the tricycle intermediate. Hydration of an alkene catalyzed by Co(acac)₂ was also employed as a key step to diastereoselectively introduce the tertiary alcohol moiety. The absolute configuration of (−)-conolutinine was established to be (2S,5aS,8aS,13aR) based on this asymmetric total synthesis.

 

 

Total Synthesis of (−)-Conolutinine

Xiangyang Feng^†‡, Guangde Jiang^‡, Zilei Xia^‡, Jiadong Hu^†‡, Xiaolong Wan^§, Jin-Ming Gao^†, Yisheng Lai^*‡, and Weiqing Xie^*†§

^† Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Science, Northwest A&F University, 22 Xinong Road, Yangling 712100, Shaanxi, China

^‡ State Key Laboratory of Natural Medicines, Jiangsu Key Laboratory of Drug Discovery for Metabolic Diseases, Center of Drug Discovery, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210009, China

^§ State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China

Org. Lett., Article ASAP

DOI: 10.1021/acs.orglett.5b02046

http://pubs.acs.org/doi/abs/10.1021/acs.orglett.5b02046

 http://pubs.acs.org/doi/suppl/10.1021/acs.orglett.5b02046/suppl_file/ol5b02046_si_001.pdf

*E-mail: yslai@cpu.edu.cn., *E-mail: xiewq@nwafu.edu.cn.

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Acyl nitroso Diels–Alder (ANDA) reaction of sorbate esters and sorbic alcohol derivatives

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We present a study of the acyl nitroso Diels–Alder (ANDA) reaction of sorbate esters and sorbic alcohol derivatives, using alkoxycarbonyl nitroso dienophiles. An optimisation of the reaction conditions for ethyl sorbate is first presented, and the product is used in an efficient synthesis of 5-methylornithine. Structure–reactivity trends in sorbic alcohol (E,E-2,4-hexadien-1-ol) and its acylated analogues are then discussed. We present single-crystal X-ray structural proof for key adducts in both series and present in detail a novel HMBC/HSQC (¹H–¹⁵N) criterion for ready distinction of regioisomers arising from such ANDA reactions.

1H–15N long-range HSQC NMR of natural 15N abundance 10e (aryl hydrogens

The acyl nitroso Diels–Alder (ANDA) reaction of sorbate derivatives: an X-ray and ¹⁵N NMR study with an application to amino-acid synthesis

Lee Bollans,^a   John Bacsa,^a   Jonathan A. Iggo,^a   Gareth A. Morris^b and   Andrew V. Stachulski*^a  

Hide Affiliations

*Corresponding authors

^aRobert Robinson Laboratories, Department of Chemistry, University of Liverpool, Liverpool, UK
E-mail: stachuls@liv.ac.uk
Fax: 44 (0) 151 794 3588
Tel: 44 (0) 151 794 3542

^bSchool of Chemistry, University of Manchester, Oxford Rd., Manchester, UK

Org. Biomol. Chem., 2009,7, 4531-4538

http://pubs.rsc.org/en/content/articlelanding/2009/ob/b912963d#!divAbstract
DOI: 10.1039/B912963D                                                                                                                                                                                                                                                                                          ///////////