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
2017-06-13T14:21:35Z (GMT)
by
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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