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6-Endo-trig radical cyclisations: Synthetic approaches to the A–B ring of (±)-forskolin

Authors :
C. Anies
Jean-Yves Lallemand
Laurent Billot
Ange Pancrazi
Source :
Tetrahedron Letters. 36:7247-7250
Publication Year :
1995
Publisher :
Elsevier BV, 1995.

Abstract

In a synthetic approach to forskolin 1 , a 6-endo-trig radical cyclisation was performed on propargylic derivative 12 to furnish in 60% yield compound 17 which contains the A-B ring system of forskolin. In the same way yn-one 14 submitted to Bu 3 SnH gave the expected cyclised product 19 in 55% yield. A particular 5-exo-dig cyclisation took place, leading to compound 18 in 10% yield, when silylated propargylic alcohol 13 was treated under the same conditions.

Details

ISSN :
00404039
Volume :
36
Database :
OpenAIRE
Journal :
Tetrahedron Letters
Accession number :
edsair.doi...........089d9cbe16e7d31f9eac7c06ac14f7bc