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Asymmetric Allylboration of vic ‐Tricarbonyl Compounds: Total Synthesis of (+)‐Awajanomycin
Author(s) -
Wohlfahrt Malte,
Harms Klaus,
Koert Ulrich
Publication year - 2011
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.201103679
Subject(s) - dihydroxylation , alkene , stereoselectivity , core (optical fiber) , stereochemistry , bicyclic molecule , chemistry , computer science , organic chemistry , enantioselective synthesis , catalysis , telecommunications
To the core : An efficient total synthesis of (+)‐awajanomycin was achieved starting with an asymmetric allylboration of a vic ‐tricarbonyl compound (see scheme; TES=triethylsilyl). A stereoselective alkene dihydroxylation followed by a differentiation of diastereotopic ester groups and a subsequent lactamization gave the bicyclic core structure.