New Methodology to Prepare Polyfunctionalized Cycloheptane Synthons, with Four Stereocenters, by Hydrolytic Cleavage of the Oxygen Bridge in C1-functionalized 8-oxabicyclic [4+3]-cycloadducts

Authors: Montana, A. M.; Garcia, F.; Batalla, C.

Source: Letters in Organic Chemistry, Volume 2, Number 5, August 2005 , pp. 475-479(5)

Publisher: Bentham Science Publishers

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Abstract:

A new synthetic methodology to obtain polyfunctionalized cycloheptane synthons, with up to four stereocenters, is presented. Three key processes are involved in this methodology: first, the synthesis of C1- functionalized 8-oxabicyclo[3.2.1]oct-6-en-3-ones by a [4+3] cycloaddition reaction; second, the stereoselective reduction of the carbonyl group on C3 and third, the hydrolytic cleavage of the oxygen bridge of the cycloadducts. This synthetic methodology is versatile enough to allow the preparation of a wide variety of polypropionate synthetic building blocks.

Keywords: cycloheptane synthons; oxabicycle; cycloadditions; functionalized furans; oxyallyl cation; polypropionate building blocks

Document Type: Review article

DOI: http://dx.doi.org/10.2174/1570178054405878

Affiliations: 1: Departamento de Quimica Organica, Universidad de Barcelona, c/ Marti i Franques 1-11, 08028- Barcelona, Spain.

Publication date: 2005-08-01

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