Novel methoxyl and hydroxyl directed pinacol rearrangements of an isocaryolane sesquiterpenoid under mitsunobu conditions

Authors
Collado, IG Hanson, JR Hernandez-Galan, R Hitchcock, PB Macias-Sanchez, AJ Racero, JC
Citation
Ig. Collado et al., Novel methoxyl and hydroxyl directed pinacol rearrangements of an isocaryolane sesquiterpenoid under mitsunobu conditions, TETRAHEDR L, 40(35), 1999, pp. 6497-6498
Citations number
11
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
35
Year of publication
1999
Pages
6497 - 6498
Database
ISI
SICI code
0040-4039(19990827)40:35<6497:NMAHDP>2.0.ZU;2-1
Abstract
Treatment of 8-methoxy-isocaryolan-9 alpha-ol (1) with acid on the one hand and with diethyl azodicarboxylate (DEAD)/triphenylphosphine on the other, leads to different pinacol rearrangements of the isocaryolane skeleton. 1S, 2S,5R,9R-8-oxo-1,4,4-trimethyltricyclo[7.2.1.0(2,5)]dodecane (2), which pos sesses a novel sesquiterpenoid skeleton, was obtained under Mitsunobu condi tions. (C) 1999 Elsevier Science Ltd. All rights reserved.