SYNTHESIS OF CARBOCYCLES VIA INTRAMOLECULAR CONJUGATE ADDITIONS - TOTAL SYNTHESES OF AXANE SESQUITERPENOIDS

Authors
GUEVEL AC HART DJ
Citation
Ac. Guevel et Dj. Hart, SYNTHESIS OF CARBOCYCLES VIA INTRAMOLECULAR CONJUGATE ADDITIONS - TOTAL SYNTHESES OF AXANE SESQUITERPENOIDS, Journal of organic chemistry, 61(2), 1996, pp. 473-479
Citations number
56
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
61
Issue
2
Year of publication
1996
Pages
473 - 479
Database
ISI
SICI code
0022-3263(1996)61:2<473:SOCVIC>2.0.ZU;2-W
Abstract
Syntheses of(+/-)-axamide-1 (2) and (+/-)-axisonitrile-1 (1) are descr ibed. The syntheses require 12 steps and 13 steps, respectively, from vinylogous ester 8 and feature the diastereoselective cyclization of u nsaturated ester 7 to perhydroindan 5. Some interesting reactions of t he organometallic derived from [(trimethylsilyl)methyl]magnesium chlor ide and cerium trichloride are also described.