Synthesis of 8-Hydroxygeraniol

Francesca M Ippoliti; Joyann S Barber; Yi Tang; Neil K Garg

doi:10.1021/acs.joc.8b01544

Synthesis of 8-Hydroxygeraniol

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

Authors

Francesca M Ippoliti¹, Joyann S Barber¹, Yi Tang¹, Neil K Garg¹

Affiliation

¹ Department of Chemistry and Biochemistry , University of California , Los Angeles , California 90095 , United States.

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

Abstract

Publication types

MeSH terms

Substances

Grants and funding