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

✍ Scribed by AndréB. Charette; Hélène Juteau

Book ID
104208125
Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
512 KB
Volume
53
Category
Article
ISSN
0040-4020

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✦ Synopsis

The chemo-and enantioselective cyclopropanation of a monoprotected bis(allylic alcohol) using a chiral dioxaborolane-derived ligand and Zn(CH2I) 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.

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