Introduction of a New Stereocenter on C1-Functionalized 8-Oxabicyclo[3.2.1] oct-6-en 3-ones by a Regio- and Stereoselective Electrophilic Addition. Obtention of Polyfunctionalized Cycloheptanes with Five Stereocenters

Author(s): A. M. Montana, F. Garcia, C. Batalla.

Journal Name: Letters in Organic Chemistry

Volume 2 , Issue 5 , 2005

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Abstract:

A methodology to obtain polyfunctionalized cycloheptane synthons, with five stereocenters, is presented. The precursors are C1-functionalized 8-oxabicyclo[3.2.1]oct-6-en-3-ones, obtained by a [4+3] cycloaddition reaction. The stereoselective reduction of the carbonyl group on C3 of these cycloadducts, followed by an electrophilic addition of organic acids on the C6-C7 double bond, under controlled conditions, allows the introduction of a new stereocenters on C6. The introduction of this new substituent on C6 takes place in a regio- and stereoselective way by a preferential exo attack on the oxabicyclic substrates. This synthetic methodology is versatile enough to allow the preparation of a wide variety of polypropionate building blocks, with applications to the synthesis of natural products with biological interest.

Keywords: cycloheptane synthons, oxabicyclo oct-en-one, electrophilic addition, cycloaddition reaction

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Article Details

VOLUME: 2
ISSUE: 5
Year: 2005
Page: [480 - 484]
Pages: 5
DOI: 10.2174/1570178054405977
Price: $65

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