First total synthesis of (+/-)-13-hydroxyneocembrene

Authors
Xing, YC Cen, W Lan, J Li, Y Li, YL
Citation
Yc. Xing et al., First total synthesis of (+/-)-13-hydroxyneocembrene, J CHIN CHEM, 46(4), 1999, pp. 595-600
Citations number
11
Categorie Soggetti
Chemistry
Journal title
JOURNAL OF THE CHINESE CHEMICAL SOCIETY
ISSN journal
00094536 → ACNP
Volume
46
Issue
4
Year of publication
1999
Pages
595 - 600
Database
ISI
SICI code
0009-4536(199908)46:4<595:FTSO(>2.0.ZU;2-0
Abstract
First total synthesis of (+/-)-13-hydroxyneocembrene (I), starting from 6-m ethyl-5-hepten-2-one (6) and geraniol (7), is described. The key steps are (i) the addition of sulfur-stabilized carbanion 12 to aldehyde 9, (ii) the synthesis of 18 by using phase-transfer catalyzed coupling reaction, and (i ii) low-valent titanium-induced intramolecular coupling of oxo aldehyde 3 t o afford the target molecule after the final deprotection.