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Updated: Jul 5, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
A stereodivergent synthesis of beta-hydroxy-alpha-methylene lactones via vinyl epoxides
Marion Davoust1, Frédéric Cantagrel, Patrick Metzner
1Laboratoire de Chimie Moléculaire et Thio-organique, ENSICAEN, Université de Caen, CNRS, 6 Boulevard du Maréchal Juin, 14050 Caen, France.
Abstract:
A catalytic diastereoselective sulfonium ylide epoxidation of aldehydes furnished original vinyl epoxides, having an MBH backbone. These highly functionalized building blocks were used for a formal synthesis of the antibiotic conocandin, and opened up a stereodivergent route towards beta-hydroxy-alpha-methylene lactones, core units of naturally occurring compounds. Under acidic conditions, the oxiranes were mainly transformed, with moderate to good yields, into trans beta-hydroxy-alpha-methylene lactones. On the other hand, a user-friendly palladium-catalysed CO2 insertion and cyclisation sequence gave the cis beta-hydroxy-alpha-methylene lactone counterparts along with an interesting cis-trans equilibration of the pi-allyl intermediates.
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