Volume 28, Issue 50
Natural Products
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ChemInform Abstract: Enantioselective Construction of Angular Triquinanes Through an Asymmetric Intramolecular Pauson-Khand Reaction. Synthesis of (+)-15- Nor-pentalenene.

J. TORMO

J. TORMO

Dep. Quim. Org., Fac. Quim., Univ. Barcelona, E-08028 Barcelona, Spain

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A. MOYANO

A. MOYANO

Dep. Quim. Org., Fac. Quim., Univ. Barcelona, E-08028 Barcelona, Spain

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M. A. PERICAS

M. A. PERICAS

Dep. Quim. Org., Fac. Quim., Univ. Barcelona, E-08028 Barcelona, Spain

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A. RIERA

A. RIERA

Dep. Quim. Org., Fac. Quim., Univ. Barcelona, E-08028 Barcelona, Spain

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First published: 02 August 2010

Abstract

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ChemInform Abstract

It is shown for the first time that a structurally complex angular triquinane, (+)-(IX), can be obtained in a short, convergent, and enantioselective manner using an intramolecular Pauson-Khand reaction in which the stereochemical control is exclusively effected by a peripheral, eliminable chiral alkoxy group. Interestingly, the absolute configuration of (+)-(IX) is the same one found in natural (+) -pentalenene.

chemical structure image

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