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Wednesday 14 January 2015

BREVICOMIN

brevicomin.gif?

6,8-Dioxabicyclo[3.2.1]octane, 7-ethyl-5-methyl-, (1R-exo)-
exo-Brevicomin
(+)-exo-brevicomin
60018-04-4 




brevicomin2.gif?


[1] Bellas, TE; Brownlee, EG;? Silverstrein, RM Tetrahedron ? 25 , 5149 .





brevicomin

epoxide to diol and diol to cyclic acetal in brevicomin
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.
brevicomin

"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 Chemie1992, 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.
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 (+)-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
* e-mail: isresck@unb.br

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, CDCl3d 0.90 (t, 7.4 Hz, 3H), 1.40 (s, 3H), 1.41-1.94 (m, 8H), 3.92 (t, 6.5 Hz, 1H), 4.12 (s large, 1H); 13C NMR (50 MHz, CDCl3d 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).


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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.


Graphical abstract: Stereoselective inversion of γ-vinyl-γ-butyrolactone under palladium catalysis: application to the synthesis of (+)-exo- and (+)-endo-brevicomins
bottom

http://pubs.rsc.org/en/content/articlelanding/2014/ra/c4ra00814f#!divAbstract


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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.
PDF (139KB)


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