Synthesis of 8-Hydroxygeraniol

J Org Chem. 2018 Sep 21;83(18):11323-11326. doi: 10.1021/acs.joc.8b01544. Epub 2018 Jul 23.

Abstract

An operationally simple protocol for the conversion of geranyl acetate to 8-hydroxygeraniol is reported. The convenient two-step procedure relies on an efficient, chemo- and regioselective SeO2-promoted oxidation, followed by straightforward deacetylation. This facile means to prepare 8-hydroxygeraniol is expected to enable biosynthetic studies pertaining to thousands of monoterpene indole alkaloids.

Publication types

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

MeSH terms

  • Chemistry Techniques, Synthetic
  • Stereoisomerism
  • Terpenes / chemical synthesis*
  • Terpenes / chemistry*

Substances

  • 8-hydroxygeraniol
  • Terpenes