有机催化对映选择性迈克尔加成-缩醛化-亨利反应串联反应，用于构建具有四个连续手性中心的六氢-6H-苯并[c]色烯酮以及阿霉素类似物的入口。
Organocatalytic Enantioselective Michael-Acetalization-Henry Reaction Cascade of 2-Hydroxynitrostyrene and 5-Oxohexanal for the Entry to the Hexahydro-6H-benzo[c]chromenones with Four Consecutive Stereogenic Centers and an Approach to Aflatoxin Analogues.
机构信息
Department of Chemistry and Biochemistry, National Chung Cheng University , Chia-Yi 621, Taiwan, R.O.C.
Instrumentation Center, National Taiwan University , Taipei 106, Taiwan, R.O.C.
出版信息
J Org Chem. 2017 Dec 1;82(23):12840-12848. doi: 10.1021/acs.joc.7b02178. Epub 2017 Nov 7.
PMID:29065686
Abstract
A domino reaction with the organocatalytic enantioselective Michael-acetalization-Henry reaction of 2-hydroxynitrostyrene and 5-oxohexanal was developed for the synthesis of hexahydro-6H-benzo[c]chromenones with four consecutive stereogenic centers and high enantioselectivity (up to >99% ee). The transformation of a NaBH-reduced adduct to the aflatoxin system via the Nef-cyclization process was achieved by the assistant of ZnBr.
摘要
发展了一种多米诺反应，通过有机催化的对映选择性迈克尔加成-缩醛化-亨利反应，将 2-羟基亚硝基苯乙烯和 5-氧代己醛进行反应，合成了具有四个连续手性中心和高对映选择性（高达>99%ee）的六氢-6H-苯并[c]色烯酮。通过 Nef 环化过程，在 ZnBr 的辅助下，将 NaBH 还原的加合物转化为黄曲霉毒素体系。
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