Total synthesis of vinigrol

Qingliang Yang; Jon T. Njardarson; Cristian Draghici; Fang Li

doi:10.1002/anie.201304624

Total synthesis of vinigrol

Qingliang Yang, Jon T. Njardarson, Cristian Draghici, Fang Li

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

64 Scopus citations

Abstract

Carbocyclic cage fight: The substrate-controlled total synthesis of vinigrol features a strategic oxidative dearomatization/Diels-Alder cycloaddition reaction and a subsequent palladium-catalyzed cyclization cascade to construct the carbocyclic core. The C4, C9, and C12 stereocenters were installed using either reduction or oxidation reactions, and the diterpenoid core was unraveled by a ring fragmentation reaction.

Original language	English (US)
Pages (from-to)	8648-8651
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	33
DOIs	https://doi.org/10.1002/anie.201304624
State	Published - Aug 12 2013
Externally published	Yes

Keywords

dearomatization
hydrogenation
natural products
terpenoids
total synthesis

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.201304624

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AU - Draghici, Cristian

AU - Li, Fang

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AB - Carbocyclic cage fight: The substrate-controlled total synthesis of vinigrol features a strategic oxidative dearomatization/Diels-Alder cycloaddition reaction and a subsequent palladium-catalyzed cyclization cascade to construct the carbocyclic core. The C4, C9, and C12 stereocenters were installed using either reduction or oxidation reactions, and the diterpenoid core was unraveled by a ring fragmentation reaction.

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KW - hydrogenation

KW - natural products

KW - terpenoids

KW - total synthesis

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Total synthesis of vinigrol

Abstract

Keywords

ASJC Scopus subject areas

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