APPLICATION OF THE CHEMOSELECTIVE AND ENANTIOSELECTIVE CYCLOPROPANATION OF POLYENES TO THE TOTAL SYNTHESIS OF (-BICYCLOHUMULENONE())

Authors
CHARETTE AB JUTEAU H
Citation
Ab. Charette et H. Juteau, APPLICATION OF THE CHEMOSELECTIVE AND ENANTIOSELECTIVE CYCLOPROPANATION OF POLYENES TO THE TOTAL SYNTHESIS OF (-BICYCLOHUMULENONE()), Tetrahedron, 53(48), 1997, pp. 16277-16286
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
48
Year of publication
1997
Pages
16277 - 16286
Database
ISI
SICI code
0040-4020(1997)53:48<16277:AOTCAE>2.0.ZU;2-F
Abstract
The chemo- and enantioselective cyclopropanation of a monoprotected bi s(allylic alcohol) using a chiral dioxaborolane-derived ligand and Zn( CH2I)(2) was used as a key step in the total synthesis of (+)-bicycloh umulenone. The synthesis of this important perfume component was effic iently accomplished in 16 steps from diethyl 3,3-dimethylglutarate in 9% overall yield. (C) 1997 Elsevier Science Ltd.