Enantioselective synthesis of the 5-6-7 carbocyclic core of the gagunin diterpenoids

Grant M Shibuya; John A Enquist Jr; Brian M Stoltz

doi:10.1021/ol401514s

Enantioselective synthesis of the 5-6-7 carbocyclic core of the gagunin diterpenoids

Org Lett. 2013 Jul 5;15(13):3480-3. doi: 10.1021/ol401514s. Epub 2013 Jun 26.

Authors

Grant M Shibuya¹, John A Enquist Jr, Brian M Stoltz

Affiliation

¹ The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Boulevard, MC 101-20, Pasadena, California 91125, USA.

Abstract

A catalytic enantioselective double allylic alkylation reaction has been employed in the synthesis of the core of the gagunin diterpenoids. Enantioenriched material was advanced in 11 steps to afford the core of the highly oxygenated target, which includes two all-carbon quaternary stereocenters.

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

Alkylation
Catalysis
Diterpenes / chemical synthesis*
Diterpenes / chemistry
Molecular Structure
Oxidants / chemistry*
Stereoisomerism

Substances

Diterpenes
Oxidants

Abstract

Publication types

MeSH terms

Substances

Grants and funding