Enantioselective formal total synthesis of (+)-aspergillide C.
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.
Panarese
Joseph D
JD
Department of Chemistry, The University of Vermont, 82 University Place, Burlington, Vermont 05405, USA.
Waters
Stephen P
SP
D001230:Aspergillus / Q000737:chemistry; D002384:Catalysis; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
D018942:Macrolides; C526624:aspergillide C; D010165:Palladium