Rhodium-catalyzed intramolecular reductive aldol-type cyclization: Application for the synthesis of a chiral necic acid lactone

Abstract
A rhodium-catalyzed intramolecular reductive aldol-type cyclization is described to give β-hydroxylactones with high diastereoselectivities. The stereoselectivity of this cyclization is highly solvent dependent and can give syn- or anti-β-hydroxylactones with high diastereoselectivity. This methodology was also applied to the synthesis of a chiral necic acid lactone which is a structural component of the pyrrolizidine alkaloid monocrotaline.

Beilstein J. Org. Chem. 2022, 18, 1642–1648. doi:10.3762/bjoc.18.176

Source: Beilstein Journal of Organic Chemistry - December 2, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: β -hydroxylactone intramolecular reductive aldol cyclization necic acid lactone rhodium catalyst Full Research Paper Source Type: research