Synthetic studies on spirovetivane phytoalexins. IV. A stereoselective synthesis of (.+-.)-3-hydroxysolavetivone.

1 January 1989

journal article
Published by Pharmaceutical Society of Japan in CHEMICAL & PHARMACEUTICAL BULLETIN

Vol. 37 (10) , 2643-2646
https://doi.org/10.1248/cpb.37.2643

Abstract

Oxidation of the silyl enol ether of (2RS, 5RS, 10RS)-6, 10-dimethyl-2-pivaloyloxyspiro[4.5]dec-6-en-8-one (5) with triphenyl phosphite ozonide (TPPO) gave stereoselectively the C₉-hydroxylated derivative (6a), which was transformed into a spirovetivane phytoalexin, (±)-3-hydroxysolavetivone (1), by a several-step sequence.

Keywords

PHOSPHITE
DEC
STEREOSELECTIVELY
PIVALOYLOXYSPIRO
SPIROVETIVANE PHYTOALEXINS
HYDROXYSOLAVETIVONE

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