?
6,8-Dioxabicyclo[3.2.1]octane, 7-ethyl-5-methyl-, (1R-exo)-
exo-Brevicomin
(+)-exo-brevicomin
60018-04-4
?
[1] Bellas, TE; Brownlee, EG;? Silverstrein, RM Tetrahedron ? 25 , 5149 .
In this scheme, the base, B:, could be C=O, R-O-R, R-OH, H2O or the conjugate base of the acid catalyst endo-Brevicomin(+)-endo-Brevicomin, the pheromone of the bark beetles such as western pine beetle、southern pine beetle and mountain pine beetle, was synthesized using lipase-catalyzed asymmetric acetylation as the key step.
"A New Synthesis of (3S, 4R)-8-Nonene-3,4-diol, the Key Intermediate for the Synthesis of (+)-endo-Brevicomin"
K. Mori and H. Kiyota, Liebigs Annalen der Chemie, 1992, 989-992 (1992).
NMR
| Reference(s) |
| Stewart, T.E., Plummer, E.L., McCandless, L.L., West, J.R., and Silverstein, R.M. 1977. J. Chem. Ecol. 3:27-43. |
| Francke, W., Schröder, F., Philipp, P., Meyer, H., Sinnwell, V., anf Gries, G. 1996. Bioorg. Med. Chem. 4:363-374. .......................................................................................................  (+)-exo-brevicomin (2), (1R,5S,7R)-7-ethyl-5-methyl-6,8-dioxabicyclo[3.2.1]octane, http://dx.doi.org/10.1590/S0103-50532002000200015
Article
Asymmetric Synthesis of exo-Isobrevicomin and exo-Brevicominvia Conjugated Addition of Primary Alkyl Iodides to a,b-Unsaturated Ketones
Andréa L. de Sousa and Inês S. Resck*
Instituto de Química, Universidade de Brasília, CP 4478, 70919-970, Brasília - DF, Brazil
http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532002000200015 Using the same conditions as above, compound 2 was prepared as a pale liquid (0.12 g, 96%); IR nmax/cm-11461, 1382, 1239, 1174, 1033 (film); 1H NMR (400 MHz, CDCl3) d 0.90 (t, J 7.4 Hz, 3H), 1.40 (s, 3H), 1.41-1.94 (m, 8H), 3.92 (t, J 6.5 Hz, 1H), 4.12 (s large, 1H); 13C NMR (50 MHz, CDCl3) d 9.8, 17.2, 25.1, 28.0, 28.6, 35.0, 78.3, 81.2, 107.7; GC/EIMS (70 eV) m/z 156 (M+, 8%), 114 (100), 98 (46), 85 (96). ...................................................................  
An efficient γ-epimerization of γ-vinyl-γ-butyrolactone is studied under palladium catalysis. The building blocks derived there in are used in an efficient stereoselective synthesis of (+)-exo- and (+)-endo-brevicomins.
  http://pubs.rsc.org/en/content/articlelanding/2014/ra/c4ra00814f#!divAbstract ......................................................................... Note | Regular issue | Vol 55, No. 4, 2001, pp.781-784 Published online:
DOI: 10.3987/COM-01-9161
■ A Concise Synthesis of (-)-endo-Brevicomin
John K. Gallos,* Loukia C. Kyradjoglou, and Theocharis V. Koftis
*Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki 540 06, Greece
Abstract
A new method for the synthesis of (-)-endo-brevicomin from D-ribose in four steps is reported.
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