A general efficient strategy for cis-3a-aryloctahydroindole alkaloids via stereocontrolled ZnBr(2)-catalyzed rearrangement of 2,3-aziridino alcohols.
A short and general approach to the cis-3a-aryloctahydroindole alkaloids has been developed on the basis of a key stereocontrolled ZnBr(2)-catalyzed rearrangement of 2,3-aziridino alcohols. Two representative members, (+/-)-crinane and (+/-)-mesembrine, have been synthesized in 15% and 11% overall yields, respectively. [reaction: see text]
Song
Zhen Lei
ZL
Department of Chemistry and State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China.
Wang
Bao Min
BM
Tu
Yong Qiang
YQ
Fan
Chun An
CA
Zhang
Shu Yu
SY
D000438:Alcohols / Q000737:chemistry*; D001388:Aziridines / Q000737:chemistry*; D002384:Catalysis; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D017967:Zinc Compounds / Q000737:chemistry*
D000438:Alcohols; D001388:Aziridines; D026121:Indole Alkaloids; D017967:Zinc Compounds