A SHORT SYNTHESIS OF THE AROMATIC MONOTERPENE ESPINTANOL

Authors
WADSWORTH DJ LOSCH S
Citation
Dj. Wadsworth et S. Losch, A SHORT SYNTHESIS OF THE AROMATIC MONOTERPENE ESPINTANOL, Tetrahedron, 50(29), 1994, pp. 8673-8676
Citations number
8
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
29
Year of publication
1994
Pages
8673 - 8676
Database
ISI
SICI code
0040-4020(1994)50:29<8673:ASSOTA>2.0.ZU;2-B
Abstract
A flexible and expedient synthesis of the leishmanicidal and trypanoci dal monoterpene espintanol 1, first isolated in 1991 from the spruce O xandra espintana, was achieved in seven steps and with an overall yiel d 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 second ary alcohol 11 to afford 1.