The enantioselective synthesis of (R)-(+)-6-isopropenyl-3-methyl-2-cycloheptenone

Journal of the Brazilian Chemical Society

Barbosa, Fernanda P.¹  Brocksom, Timothy J.¹  Brocksom, Ursula¹  Universidade Federal de São Carlos, São Carlos, Brazil¹ 

关键词: cycloheptenone;    carvone;    ring expansion;    perhydroazulene;    enantioselectivity;   

DOI  :  10.1590/S0103-50532006000400023

学科分类：化学（综合）

来源: SciELO

【 摘 要 】

(R)-(+)-6-isopropenyl-3-methyl-2-cycloheptenone is synthesized from (R)-(-)-carvone by reduction and trialkylsilyl-enolether formation, cyclopropanation with methylene iodide and diethylzinc, followed by a Saegusa type oxidation with ferric chloride and finally dehydrochlorination with base. The title compound is obtained in five steps and 38% overall yield, being a useful chiron for guaiane sesquiterpene natural products.

【 授权许可】

Unknown