Synthesis of (+)-Cladospolide C.
(+)-Cladospolide C was synthesized in eight steps with 5% total yield, using methyl acrylate, (3R,4R)-1,5-hexadiene-3,4-diol, and (6R)-6-hepten-2-ol as the starting materials. Two cross-metathesis reactions and Yamaguchi esterification were applied to assemble the three units into (+)-Cladospolide C. Unsuccessful routes using ring-closing metathesis are also discussed.
Chou
Chun-Yi
CY
Department of Chemistry, National Central University, Jung-Li City, Taoyuan, Taiwan 320.
Hou
Duen-Ren
DR
D000179:Acrylates / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
D000179:Acrylates; D018942:Macrolides; C492938:cladospolide C; C035956:methyl acrylate