Application of the chemo- and enantioselective cyclopropanation of polyenes to the total synthesis of (+)-bicyclohumulenone

The chemo- and enantioselective cyclopropanation of a monoprotected bis(allylic alcohol) using a chiral dioxaborolane-derived ligand and Zn(CH 2I) 2 was used as a key step in the total synthesis of (+)-bicyclohumulenone. The synthesis of this important perfume component was efficiently accomplished...

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Bibliographic Details
Published in:Tetrahedron 1997-12, Vol.53 (48), p.16277-16286
Main Authors: Charette, AndréB., Juteau, Hélène
Format: Article
Language:English
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Summary:The chemo- and enantioselective cyclopropanation of a monoprotected bis(allylic alcohol) using a chiral dioxaborolane-derived ligand and Zn(CH 2I) 2 was used as a key step in the total synthesis of (+)-bicyclohumulenone. The synthesis of this important perfume component was efficiently accomplished in 16 steps from diethyl 3,3-dimethylglutarate in 9% overall yield. The synthesis was efficiently accomplished in 16 steps from diethyl 3,3-dimethylglutarate in 9% overall yield.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(97)01014-4