Organocatalytic Enantioselective Michael–Acetalization–Reduction–Nef Reaction for a One-Pot Entry to the Functionalized Aflatoxin System. Total Synthesis of (−)- Dihydroaflatoxin D2 and (−)- and (+)-Microminutinin

An efficient method has been developed for the enantioselective synthesis of the aflatoxin system with multiple stereocenters via a sequence of organocatalytic Michael–acetalization–reduction–Nef reactions that proceed with high enantioselectivities (90–99% ee). The one-pot reaction sequence provide...

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Published inOrganic letters Vol. 19; no. 13; pp. 3494 - 3497
Main Authors Huang, Wei-Lun, Raja, Arun, Hong, Bor-Cherng, Lee, Gene-Hsiang
Format Journal Article
LanguageEnglish
Published American Chemical Society 07.07.2017
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Summary:An efficient method has been developed for the enantioselective synthesis of the aflatoxin system with multiple stereocenters via a sequence of organocatalytic Michael–acetalization–reduction–Nef reactions that proceed with high enantioselectivities (90–99% ee). The one-pot reaction sequence provides a facile entry to the aflatoxin system, including dihydroaflatoxin D2, which includes a formal total synthesis of aflatoxin B2. The first total synthesis of (−)- and (+)-microminutinin was also achieved via this protocol.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b01473