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ChemInform Abstract: Stereochemistry of Epoxidation of Some Caryophyllenols.

✍ Scribed by I. G. COLLADO; J. R. HANSON; P. B. HITCHCOCK; A. J. MACIAS-SANCHEZ

Publisher
John Wiley and Sons
Year
2010
Weight
33 KB
Volume
28
Category
Article
ISSN
0931-7597

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✦ Synopsis

In order to shed some light on the consequence of the variable conformations of the nine-membered ring of the sesquiterpene caryophyllene the epoxidation of allylic alcohols and their subsequent tetracyanoethylene-catalyzed solvolysis are investigated.The formation of trans-epoxides by syn-epoxidation is a consequence of the conformational flexibility of the nine-membered ring, which places the alcohol at C-5 close to the Ξ±-face of the endo-alkene in (III) and close to the Ξ²-face in (I) and (V). -(COLLADO, I.

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