A SYNTHETIC APPROACH TO (+ -)-FORSKOLIN .2. RADICAL APPROACHES OF THEAB RING-SYSTEM AND FORMAL SYNTHESIS OF (+/-)-FORSKOLIN/

Authors
ANIES C PANCRAZI A LALLEMAND JY PRANGE T
Citation
C. Anies et al., A SYNTHETIC APPROACH TO (+ -)-FORSKOLIN .2. RADICAL APPROACHES OF THEAB RING-SYSTEM AND FORMAL SYNTHESIS OF (+/-)-FORSKOLIN/, Bulletin de la Societe chimique de France, 134(2), 1997, pp. 203-222
Citations number
62
Categorie Soggetti
Chemistry Inorganic & Nuclear",Biology,Chemistry
Journal title
Bulletin de la Societe chimique de France → ACNP
ISSN journal
00378968
Volume
134
Issue
2
Year of publication
1997
Pages
203 - 222
Database
ISI
SICI code
0037-8968(1997)134:2<203:ASAT(->2.0.ZU;2-S
Abstract
A 6-endo-trig cyclization was performed from enzymes 8 and 10 usingBu( 3)SnH/AIBN, leading to the construction of the trans-decalinic AB ring system of (+/-)-forskolin 1. In a second radical approach to (+/-)-fo rskolin 1, the diol 31 was oxidized to dialdehyde 6. A pinacolic coupl ing reaction promoted by SmI2 then delivered the cyclized 6 beta,7 bet a-diol 41. From this compound the unsaturated lactone 2 was then prepa red leading to a formal synthesis of (+/-)-forskolin 1.