The first total synthesis of (+/-)-junicedranol based on a novel anionic [1,3] rearrangement

Authors
Uyehara, T Sato, Y Ishizuka, H Sakiyama, Y Ueno, M Sato, T
Citation
T. Uyehara et al., The first total synthesis of (+/-)-junicedranol based on a novel anionic [1,3] rearrangement, TETRAHEDR L, 41(12), 2000, pp. 1939-1942
Citations number
13
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
12
Year of publication
2000
Pages
1939 - 1942
Database
ISI
SICI code
0040-4039(20000318)41:12<1939:TFTSO(>2.0.ZU;2-V
Abstract
The racemate of junicedranol, a sesquiterpene-alcohol with a novel carbon s keleton, was prepared through a unique anionic [1,3] rearrangement of an 8- methylenebicyclo[3.2.1]oct-6-en-2-ol giving a cyclopentadiene derivative an d the facial- and regioselective Diels-Alder reaction of the cyclopentadien e with a ketene equivalent leading to the junicedranol framework. (C) 2000 Elsevier Science Ltd. All rights reserved.