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Enantioselective Total Synthesis of Amphidinolide F
Author(s) -
Mahapatra Subham,
Carter Rich G.
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201203935
Subject(s) - enantioselective synthesis , chemistry , umpolung , polyketide , tetrahydrofuran , sulfone , total synthesis , alkylation , aldehyde , stereochemistry , lithium (medication) , combinatorial chemistry , organic chemistry , catalysis , psychology , solvent , biosynthesis , nucleophile , enzyme , psychiatry
A common‐intermediate approach is utilized in the total synthesis of amphidinolide F (see scheme, left) to access both the C1–C8 and the C18–C25 portions of the macrolide. A silver‐catalyzed rearrangement/cyclization was employed to construct the two tetrahydrofuran rings. A Felkin‐controlled, dienyl lithium addition to an α‐chiral aldehyde incorporated both the C9–C11 diene and the alcohol at C8. An umpolung sulfone alkylation/oxidative desulfurization sequence is employed to couple the two moieties.