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A short synthesis of the aromatic monoterpene espintanol

Authors :
David J. Wadsworth
Sabine Losch
Source :
Tetrahedron. 50:8673-8676
Publication Year :
1994
Publisher :
Elsevier BV, 1994.

Abstract

A flexible and expedient synthesis of the leishmanicidal and trypanocidal monoterpene espintanol 1 , first isolated in 1991 from the spruce Oxandra espintana , was achieved in seven steps and with an overall yield of 11%. Key steps were the direct conversion of the methyl ester 6b to the methyl ketone 7 upon treatment with methyl lithium and the acid-catalyzed benzylic hydroperoxide rearrangement reaction of the secondary alcohol 11 to afford 1 .

Details

ISSN :
00404020
Volume :
50
Database :
OpenAIRE
Journal :
Tetrahedron
Accession number :
edsair.doi...........04b0b37ed566ac71df83fac9621e89c5