An efficient substrate-controlled approach towards hypoestoxide, a member of a family of diterpenoid natural products with an inside-out [9.3.1]bicyclic core

Nicholas A. McGrath; Christopher A. Lee; Hiroshi Araki; Matthew Brichacek; Jon T. Njardarson

doi:10.1002/anie.200804237

An efficient substrate-controlled approach towards hypoestoxide, a member of a family of diterpenoid natural products with an inside-out [9.3.1]bicyclic core

Nicholas A. McGrath, Christopher A. Lee, Hiroshi Araki, Matthew Brichacek, Jon T. Njardarson

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

21 Scopus citations

Abstract

(Chemical Equation Presented) The bicycle works: A versatile route to the verticillane family of natural products has been devised, utilizing a strategically rigidified relay ring-closing metathesis reaction. The shape of the bicyclic product was used to stereoselectively control the bisepoxidation reaction towards hypoestoxide, a member of this natural product family.

Original language	English (US)
Pages (from-to)	9450-9453
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	47
Issue number	49
DOIs	https://doi.org/10.1002/anie.200804237
State	Published - Nov 24 2008
Externally published	Yes

Keywords

Atropisomerism
Cyclization
Hypoestoxide
Natural products
Total synthesis

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.200804237

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An efficient substrate-controlled approach towards hypoestoxide, a member of a family of diterpenoid natural products with an inside-out [9.3.1]bicyclic core. / McGrath, Nicholas A.; Lee, Christopher A.; Araki, Hiroshi et al.
In: Angewandte Chemie - International Edition, Vol. 47, No. 49, 24.11.2008, p. 9450-9453.

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

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AU - Brichacek, Matthew

AU - Njardarson, Jon T.

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An efficient substrate-controlled approach towards hypoestoxide, a member of a family of diterpenoid natural products with an inside-out [9.3.1]bicyclic core

Abstract

Keywords

ASJC Scopus subject areas

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