A general efficient strategy for cis-3a-aryloctahydroindole alkaloids via stereocontrolled ZnBr(2)-catalyzed rearrangement of 2,3-aziridino alcohols

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 y...

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Veröffentlicht in:Organic letters 2003-06, Vol.5 (13), p.2319-2321
Hauptverfasser: Song, Zhen Lei, Wang, Bao Min, Tu, Yong Qiang, Fan, Chun An, Zhang, Shu Yu
Format: Artikel
Sprache:eng
Schlagworte:
Alcohols - chemistry
Aziridines - chemistry
Catalysis
Indole Alkaloids - chemical synthesis
Indole Alkaloids - chemistry
Stereoisomerism
Zinc Compounds - chemistry
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Zusammenfassung: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]
ISSN:1523-7060