Total Syntheses of the Resorcylic Acid Lactone Neocosmosin A and Its Enantiomer | Zendy

Yiwen Zhang | Zendy; Michael Dlugosch | Zendy; Martin Jübermann | Zendy; Martin G. Banwell | Zendy; Jas S. Ward | Zendy

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Total Syntheses of the Resorcylic Acid Lactone Neocosmosin A and Its Enantiomer

Author(s) -

Yiwen Zhang,

Michael Dlugosch,

Martin Jübermann,

Martin G. Banwell,

Jas S. Ward

Publication year - 2015

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.5b00590

Subject(s) - chemistry , lactone , ring closing metathesis , metathesis , total synthesis , enantiomer , mitsunobu reaction , stereochemistry , natural product , olefin metathesis , palladium , enantioselective synthesis , organic chemistry , catalysis , polymerization , polymer

A total synthesis of the structure, 1, assigned to the recently reported resorcylic acid lactone (RAL) neocosmosin A has been established. Olefin-cross metathesis, ring-closing metathesis, palladium-catalyzed Meinwald rearrangement, and Mitsunobu esterification reactions were used as key steps. A late-stage and simple modification to the reaction sequence also provided compound ent-1 that, in fact, represents the true structure of the natural product.

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