Enantioselective total synthesis of aspergillide C.
The first enantioselective total synthesis of aspergillide C, a cytotoxic 14-membered macrolide isolated from the marine-derived fungus Aspergillus ostianus, has been accomplished from a commercially available chiral glycidol derivative by a 12-step sequence involving an expeditious preparation of a cyclic acetal intermediate and a trans-selective Ferrier-type two-carbon homologation reaction.
Nagasawa
Tomohiro
T
Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University, Tsutsumidori-Amamiyamachi, Aoba-ku, Sendai 981-8555, Japan.
Kuwahara
Shigefumi
S
D004852:Epoxy Compounds / Q000737:chemistry*; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism
D004852:Epoxy Compounds; D018942:Macrolides; D020005:Propanols; C526624:aspergillide C; C004312:glycidol