CASCADE RADICAL CYCLIZATIONS LEADING TO POLYCYCLIC DITERPENES - TOTALSYNTHESIS OF (+ -)-SPONGIAN-16-ONE/

Authors
PATTENDEN G ROBERTS L BLAKE AJ
Citation
G. Pattenden et al., CASCADE RADICAL CYCLIZATIONS LEADING TO POLYCYCLIC DITERPENES - TOTALSYNTHESIS OF (+ -)-SPONGIAN-16-ONE/, Journal of the Chemical Society. Perkin transactions. I, (5), 1998, pp. 863-868
Citations number
33
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
5
Year of publication
1998
Pages
863 - 868
Database
ISI
SICI code
0300-922X(1998):5<863:CRCLTP>2.0.ZU;2-S
Abstract
A cascade of three consecutive 6-endo-trig radical cyclisations from t he polyene acyl radical intermediate 12 derived from the selenoate 11 is used to construct the trans,anti,trans,anti,cis-tetracyclic keto la ctone 20 in one step. Manipulation of the ketone function in 20 to the corresponding gem-dimethyl substituted carbon then completed a concis e synthesis of the marine metabolite spongian-16-one 1.