1038783-21-9Relevant articles and documents
A stereodivergent synthesis of β-hydroxy-α-methylene lactones via vinyl epoxides
Davoust, Marion,Cantagrel, Frederic,Metzner, Patrick,Briere, Jean-Francois
experimental part, p. 1981 - 1993 (2009/01/31)
A catalytic diastereoselective sulfonium ylide epoxidation of aldehydes furnished original vinyl epoxides, having an MBH backbone. These highly functionalised building blocks were used for a formal synthesis of the antibiotic conocandin, and opened up a stereodivergent route towards β-hydroxy-α-methylene lactones, core units of naturally occurring compounds. Under acidic conditions, the oxiranes were mainly transformed, with moderate to good yields, into trans β-hydroxy-α-methylene lactones. On the other hand, a user-friendly palladium-catalysed CO2 insertion and cyclisation sequence gave the cis β-hydroxy-α-methylene lactone counterparts along with an interesting cis-trans equilibration of the π-allyl intermediates. The Royal Society of Chemistry.