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 in | Organic letters Vol. 19; no. 13; pp. 3494 - 3497 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
American Chemical Society
07.07.2017
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Online Access | Get full text |
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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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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/acs.orglett.7b01473 |