Is a 1,4-Alkyl Shift Involved in the Biosynthesis of Ledol and Viridiflorol?

J Org Chem. 2017 Apr 7;82(7):3957-3959. doi: 10.1021/acs.joc.7b00187. Epub 2017 Mar 15.

Abstract

Results from density functional theory computations indicate that a 1,4-alkyl shift proposed as part of the carbocation cyclization/rearrangement leading to ledol, viridiflorol, and related sesquiterpenes is not energetically viable. Instead, a previously proposed mechanism that avoids such a shift is greatly preferred.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Cyclization
  • Sesquiterpenes / metabolism*
  • Stereoisomerism
  • Terpenes / metabolism*

Substances

  • Sesquiterpenes
  • Terpenes
  • ledol
  • viridiflorol