Enantioselective Total Synthesis of (−)-Maoecrystal V

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 stereos...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2014-12, Vol.136 (51), p.17750-17756
Main Authors: Zheng, Changwu, Dubovyk, Igor, Lazarski, Kiel E, Thomson, Regan J
Format: Article
Language:English
Subjects:
Amines - chemistry
Cyclization
Cycloaddition Reaction
Diterpenes - chemical synthesis
Diterpenes - chemistry
Oxidation-Reduction
Stereoisomerism
Substrate Specificity
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja5109694