Volume 44, Issue 34
Heterocyclic Compounds

ChemInform Abstract: Versatile Approaches for the Synthesis of Fused-Ring γ-Lactones Utilizing Cyclopropane Intermediates.

Timothy R. Newhouse

Timothy R. Newhouse

Dep. Chem. Chem. Biol., Harvard Univ., Cambridge, MA 02138, USA

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Philip S. J. Kaib

Philip S. J. Kaib

Dep. Chem. Chem. Biol., Harvard Univ., Cambridge, MA 02138, USA

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Andrew W. Gross

Andrew W. Gross

Dep. Chem. Chem. Biol., Harvard Univ., Cambridge, MA 02138, USA

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E. J. Corey

E. J. Corey

Dep. Chem. Chem. Biol., Harvard Univ., Cambridge, MA 02138, USA

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First published: 01 August 2013

Abstract

Five sequences demonstrate the usefulness for the construction of a range of bi- and tricyclic functionalized lactones with control of stereochemistry and a minimum of synthetic steps, involving an acid-catalyzed cyclopropylester to γ-lactone skeletal rearrangement.

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