0

β-Ketoesters as Mono- Or Bisnucleophiles: A Concise Enantioselective Total Synthesis of (-)-Englerin A and B

Lei Guo, Bernd Plietker

Angew Chem Int Ed Engl. 2019 Jun 17;58(25):8346-8350.

PMID: 30938023

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP1094250131 (-)-Englerin B (-)-Englerin B 1094250-13-1 Price
qrcode