Biomimetic synthesis of arteannuin H and the 3,2-rearrangement of allylic hydroperoxides

Authors
Sy, LK Ngo, KS Brown, GD
Citation
Lk. Sy et al., Biomimetic synthesis of arteannuin H and the 3,2-rearrangement of allylic hydroperoxides, TETRAHEDRON, 55(52), 1999, pp. 15127-15140
Citations number
25
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
52
Year of publication
1999
Pages
15127 - 15140
Database
ISI
SICI code
0040-4020(199912)55:52<15127:BSOAHA>2.0.ZU;2-R
Abstract
The acyl endoperoxide arteannuin H, recently reported as a novel natural pr oduct from Artemisia annua, has been obtained in two steps from the photoox idation of dihydroartemisinic acid, thereby confirming biogenetic speculati on regarding its derivation from a secondary allylic hydroperoxide. The lit tle studied 3,2-rearrangement reaction of such allylic hydroperoxides is al so discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.