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Formal synthesis of leustroducsin B via Reformatsky/Claisen condensation of silyl glyoxylates.

ABSTRACT: A formal synthesis of leustroducsin B has been completed. The synthesis relies upon a recently developed Reformatsky/Claisen condensation of silyl glyoxylates and enantioenriched ?-lactones that establishes two of the molecule's three core stereocenters and permits further elaboration to an intermediate in Imanishi's synthesis via reliable chemistry (Prasad reduction, asymmetric pentenylation, Mitsunobu inversion).

SUBMITTER: Greszler SN

PROVIDER: S-EPMC3115596 | biostudies-literature | 2011 Jun

REPOSITORIES: biostudies-literature

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Formal synthesis of leustroducsin B via Reformatsky/Claisen condensation of silyl glyoxylates.

Greszler Stephen N SN Malinowski Justin T JT Johnson Jeffrey S JS

Organic letters 20110517 12

A formal synthesis of leustroducsin B has been completed. The synthesis relies upon a recently developed Reformatsky/Claisen condensation of silyl glyoxylates and enantioenriched β-lactones that establishes two of the molecule's three core stereocenters and permits further elaboration to an intermediate in Imanishi's synthesis via reliable chemistry (Prasad reduction, asymmetric pentenylation, Mitsunobu inversion). ...[more]

PMID: 21591684

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