Total syntheses of the resorcylic acid lactone neocosmosin a and its enantiomer

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

doi:10.1021/acs.joc.5b00590

Total syntheses of the resorcylic acid lactone neocosmosin a and its enantiomer

Yiwen Zhang
, Michael Dlugosch
, Martin Jübermann
, Martin G. Banwell^*
, Jas S. Ward

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

25 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	4828-4833
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	80
Issue number	9
DOIs	https://doi.org/10.1021/acs.joc.5b00590
Publication status	Published - 1 May 2015

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abstract = "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.",

author = "Yiwen Zhang and Michael Dlugosch and Martin J{\"u}bermann and Banwell, \{Martin G.\} and Ward, \{Jas S.\}",

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AU - Zhang, Yiwen

AU - Dlugosch, Michael

AU - Jübermann, Martin

AU - Banwell, Martin G.

AU - Ward, Jas S.

PY - 2015/5/1

Y1 - 2015/5/1

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/84928910864

U2 - 10.1021/acs.joc.5b00590

DO - 10.1021/acs.joc.5b00590

M3 - Article

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 9

ER -

Total syntheses of the resorcylic acid lactone neocosmosin a and its enantiomer

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