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Enantioselective formal total synthesis of (+)-aspergillide C.

ABSTRACT: An enantioselective formal total synthesis of the cytotoxic macrolide (+)-aspergillide C has been accomplished from (S)-(-)-glyceraldehyde acetonide and the Danishefsky-Kitahara diene. Strategic transformations include a hetero Diels-Alder reaction, Ferrier-type addition, and palladium-catalyzed oxidative lactonization to set key stereocenters within the dihydropyran core, followed by fragment coupling via (E)-selective Julia-Kocienski olefination.

SUBMITTER: Panarese JD 

PROVIDER: S-EPMC2783990 | biostudies-literature | 2009 Nov

REPOSITORIES: biostudies-literature

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Enantioselective formal total synthesis of (+)-aspergillide C.

Panarese Joseph D JD   Waters Stephen P SP  

Organic letters 20091101 21

An enantioselective formal total synthesis of the cytotoxic macrolide (+)-aspergillide C has been accomplished from (S)-(-)-glyceraldehyde acetonide and the Danishefsky-Kitahara diene. Strategic transformations include a hetero Diels-Alder reaction, Ferrier-type addition, and palladium-catalyzed oxidative lactonization to set key stereocenters within the dihydropyran core, followed by fragment coupling via (E)-selective Julia-Kocienski olefination. ...[more]

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