STEREOCONTROLLED SYNTHESIS OF ANGULARLY FUSED TRICYCLIC SYSTEMS BY TIN-MEDIATED RADICAL CYCLIZATION

Authors
JANARDHANAM S SHANMUGAM P RAJAGOPALAN K
Citation
S. Janardhanam et al., STEREOCONTROLLED SYNTHESIS OF ANGULARLY FUSED TRICYCLIC SYSTEMS BY TIN-MEDIATED RADICAL CYCLIZATION, Journal of organic chemistry, 58(27), 1993, pp. 7782-7788
Citations number
59
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
58
Issue
27
Year of publication
1993
Pages
7782 - 7788
Database
ISI
SICI code
0022-3263(1993)58:27<7782:SSOAFT>2.0.ZU;2-G
Abstract
Two efficient pathways for the stereocontrolled synthesis of functiona lized, angularly fused tricyclic carbocycles from readily available 2- formylcycloalkanones are described. Tricyclo[7.4.0.0(4,9)]tridecane 13 , tricyclo[7.5.0.0(4,9)]tetradecane 16, and tricyclo[7.3.0.0(4,9)]dode canes 20 and 21 were synthesized by means of path A. Path B is highly convergent, is 95% stereoselective, and leads to a tricyclo-[7.4.0.0(4 ,9)]tridecane skeleton 29.