Studies on the synthesis of the decahydro-as-indacene ring system of (-)-spinosyn A via transannular Diels-Alder reactions of substituted (E,E,E)-cyclododeca-1,6,8-trienes

Authors
Frank, SA Works, AB Roush, WR
Citation
Sa. Frank et al., Studies on the synthesis of the decahydro-as-indacene ring system of (-)-spinosyn A via transannular Diels-Alder reactions of substituted (E,E,E)-cyclododeca-1,6,8-trienes, CAN J CHEM, 78(6), 2000, pp. 757-771
Citations number
77
Categorie Soggetti
Chemistry
Journal title
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE
ISSN journal
00084042 → ACNP
Volume
78
Issue
6
Year of publication
2000
Pages
757 - 771
Database
ISI
SICI code
0008-4042(200006)78:6<757:SOTSOT>2.0.ZU;2-E
Abstract
Stereoselective syntheses of decahydro-as-indacenes 31 and 54 are reported. The key features of our syntheses of 31 and 54 are the tandem Ireland-Clai sen ring contraction of lactones 29 and 38 followed by the transannular Die ls-Alder cyclization of cyclododecatrienes 30 and 35. Transition state mode ling of both the transannular Diels-Alder reaction and the Ireland-Claisen ring contraction using PCModel is also described.