The first total synthesis of (+/-)-2-thiocyanatoneo pupukeanane based on apinacol-type rearrangement

Authors
Uyehara, T Onda, K Nozaki, N Karikomi, M Ueno, M Sato, T
Citation
T. Uyehara et al., The first total synthesis of (+/-)-2-thiocyanatoneo pupukeanane based on apinacol-type rearrangement, TETRAHEDR L, 42(4), 2001, pp. 699-702
Citations number
10
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
4
Year of publication
2001
Pages
699 - 702
Database
ISI
SICI code
0040-4039(20010122)42:4<699:TFTSO(>2.0.ZU;2-6
Abstract
The racemic mixture of 2-thiocyanatoneopupukeanane, a marine sesquiterpene- thiocyanate with a tricylo[4.3.1.0(3.7)]decane skeleton, was prepared throu gh a pinacol-type rearrangement of a bicyclo[2.2.2]oct-5-en-2-ol giving a b icyclo[3.2.1]oct-6-en-2-one derivative and an aldol reaction leading to the neopupukeanane framework. (C) 2001 Elsevier Science Ltd. All rights reserv ed.