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Total Synthesis of Marinomycin A Based on a Direct Dimerization Strategy
Author(s) -
Nishimaru Tatsuya,
Kondo Masashi,
Takeshita Kimito,
Takahashi Keisuke,
Ishihara Jun,
Hatakeyama Susumi
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201404408
Subject(s) - total synthesis , monomer , chemistry , stereochemistry , transesterification , enantioselective synthesis , strain (injury) , combinatorial chemistry , organic chemistry , catalysis , biology , polymer , anatomy
Abstract The asymmetric total synthesis of (+)‐marinomycin A, a 44‐membered macrodiolide antitumor agent and antibiotic isolated from a marine actinomycete, Marinispora strain CNQ‐140, is reported. The key features of the synthesis include the highly convergent stereocontrolled construction of the monomeric hydroxy salicylate starting from asymmetric epoxidation of the σ‐symmetrical dialkenyl carbinol, and an unprecedented direct dimerization through NaHMDS‐promoted double transesterification.