Premium
β‐Ketoesters as Mono‐ or Bisnucleophiles: A Concise Enantioselective Total Synthesis of (−)‐Englerin A and B
Author(s) -
Guo Lei,
Plietker Bernd
Publication year - 2019
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.201900401
Subject(s) - enantioselective synthesis , total synthesis , chemistry , moiety , cycloaddition , aldol reaction , hydrosilylation , stereochemistry , cyclopentenone , yield (engineering) , swern oxidation , kinetic resolution , michael reaction , organic chemistry , combinatorial chemistry , catalysis , dimethyl sulfoxide , materials science , metallurgy
A short enantioselective total synthesis of englerin A, a guaiane sesquiterpene with significant in vitro antitumor activity, is reported. Key features of this total synthesis are an organocatalytic asymmetric decarboxylative aldol reaction, a neighboring‐group‐participating [4+3] cycloaddition, a novel one‐pot Heck coupling/regioselective 1,4‐hydrosilylation/Tamao–Fleming oxidation cascade, and a kinetic CBS reduction, generating the optically pure natural product in 6.7 % overall yield over twelve steps starting from methylglyoxal. Selective saponification of the more reactive glycolic ester moiety of englerin A also gave (−)‐englerin B.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom