Enantioselective total synthesis of (-)-maoecrystal v

Changwu Zheng; Igor Dubovyk; Kiel E. Lazarski; Regan J. Thomson

doi:10.1021/ja5109694

Enantioselective total synthesis of (-)-maoecrystal v

Changwu Zheng, Igor Dubovyk, Kiel E. Lazarski, Regan J. Thomson^*

^*Corresponding author for this work

Chemistry

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

71 Scopus citations

Abstract

The enantioselective synthesis of maoecrystal V, a cytotoxic polycyclic diterpene, is described. Key reactions in the synthesis include an intramolecular Heck reaction, an oxidative cycloetherification, and an intermolecular Diels-Alder reaction to forge the carbocyclic core in a concise and stereoselective manner. Late-stage amine and C-H oxidation is used to install the final functional groups required to complete the synthesis.

Original language	English (US)
Pages (from-to)	17750-17756
Number of pages	7
Journal	Journal of the American Chemical Society
Volume	136
Issue number	51
DOIs	https://doi.org/10.1021/ja5109694
State	Published - Dec 24 2014

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja5109694

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abstract = "The enantioselective synthesis of maoecrystal V, a cytotoxic polycyclic diterpene, is described. Key reactions in the synthesis include an intramolecular Heck reaction, an oxidative cycloetherification, and an intermolecular Diels-Alder reaction to forge the carbocyclic core in a concise and stereoselective manner. Late-stage amine and C-H oxidation is used to install the final functional groups required to complete the synthesis.",

author = "Changwu Zheng and Igor Dubovyk and Lazarski, {Kiel E.} and Thomson, {Regan J.}",

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AU - Zheng, Changwu

AU - Dubovyk, Igor

AU - Lazarski, Kiel E.

AU - Thomson, Regan J.

PY - 2014/12/24

Y1 - 2014/12/24

N2 - The enantioselective synthesis of maoecrystal V, a cytotoxic polycyclic diterpene, is described. Key reactions in the synthesis include an intramolecular Heck reaction, an oxidative cycloetherification, and an intermolecular Diels-Alder reaction to forge the carbocyclic core in a concise and stereoselective manner. Late-stage amine and C-H oxidation is used to install the final functional groups required to complete the synthesis.

AB - The enantioselective synthesis of maoecrystal V, a cytotoxic polycyclic diterpene, is described. Key reactions in the synthesis include an intramolecular Heck reaction, an oxidative cycloetherification, and an intermolecular Diels-Alder reaction to forge the carbocyclic core in a concise and stereoselective manner. Late-stage amine and C-H oxidation is used to install the final functional groups required to complete the synthesis.

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Enantioselective total synthesis of (-)-maoecrystal v

Abstract

ASJC Scopus subject areas

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