Cascade Polycyclization: Exploration of a Convergent Route to Access Various Tricyclic and Tetracyclic Products Related to Sterols

16 July 2003

journal article
Published by American Chemical Society (ACS) in The Journal of Organic Chemistry

Vol. 68 (16) , 6140-6148
https://doi.org/10.1021/jo034280n

Abstract

The expedient synthesis of tricyclic and tetracyclic compounds via a cascade polycyclization methodology is described. Nazarov substrates (II) containing two Michael acceptors and a cyclohexenone ester (I) underwent cycloaddition followed by intramolecular 1,4-addition to furnish, in a highly stereoselective manner, tricyclic and tetracyclic products (III). Such compounds are interesting intermediates for the synthesis of polycyclic natural and unnatural products.

Keywords

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