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

Title: 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

Volume: 2 Issue: 5

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

Affiliation:

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

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.

Cite this article as:

Montana M. A., Garcia F. and Batalla C., 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, Letters in Organic Chemistry 2005; 2 (5) . https://dx.doi.org/10.2174/1570178054405977