Enantioselective Cascade Sequence to Indoloquinolizidines and Its Application in the Synthesis of epi-Geissochizol

An organocatalyzed one-pot Michael addition and Pictet-Spengler sequence utilizing beta-keto amide and aliphatic alpha,beta-unsaturated aldehydes was developed, which provided access to highly substituted indolo[2,3-a]quinolizidines as a mixture of keto and enol tautomers. Such tautomeric pairs were...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 22; pp. 3675 - 3679
Main Authors Wu, Xiaoyu, Zhang, Yao, Dai, Xiaoyang, Fang, Huihui, Chen, Jie, Cao, Weiguo, Zhao, Gang
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.11.2011
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Michael addition
organocatalysis
enantioselectivity
9-METHOXYGEISSOSCHIZOL
CONCISE
LACTAM
ISOMERIZATION
INDOLE-DERIVATIVES
reduction
MITRAGYNINE
cyclization
ALKALOIDS
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Summary:An organocatalyzed one-pot Michael addition and Pictet-Spengler sequence utilizing beta-keto amide and aliphatic alpha,beta-unsaturated aldehydes was developed, which provided access to highly substituted indolo[2,3-a]quinolizidines as a mixture of keto and enol tautomers. Such tautomeric pairs were transformed into stable compounds with an E-ethylidenyl group in telescoped steps. This method was successfully applied in the synthesis of epi-geissoschizol.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0030-1260243