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- Title
Synthesis of (±)-Kempa-6,8-dien-3-ol (=(2aRS,3SR,4aSR,7RS,7aSR,10bSR,10cSR)-2,2a,3,4,4a,5,6,7,7a,8,10b,10c-Dodecahydro-2a,7,10,10c-tetramethylnaphth[2,18-cde]azulen-3-ol) ( Part 63 of the series Cyclization of Polyenes; for Part 62, see [1].).
- Authors
Tadahiro Kato; Motoyuki Tanaka; Shin-suke Takagi; Keita Nakanishi; Masahiro Hoshikawa
- Abstract
The synthesis of kempa-6,8-dien-3β-ol (4a), as a synthetic leading model of the natural product 4b, was carried out starting from intermediate 12, the synthetic route of which has been developed previously (Scheme 1). The conversion of 12 to the model compound 4a involved the elaboration of three structure modifications by three processes, Tasks A, B, and C (see Scheme 2). Task A was achieved by epoxy-ring opening of 41 with Me3SiCl (Scheme 9), and Task B being performed by oxidation at the 13-position, followed by hydrogenation, and then epimerization (Schemes 4 and 5). The removal of the 2-OH group from 12 (Task C) was achieved via 30b according to Scheme 6, whereby 30b was formed exclusively from 30a/31a 1 : 1 (Scheme 7). In addition, some useful reactions from the synthetic viewpoint were developed during the course of the present experiments.
- Subjects
NATURAL products; HYDROGENATION; OXIDATION; RING formation (Chemistry)
- Publication
Helvetica Chimica Acta, 2004, Vol 87, Issue 1, p197
- ISSN
0018-019X
- Publication type
Article