An efficient formal synthesis of (-)-clavosolide a featuring a "mismatched" stereoselective oxocarbenium reduction.
The enantioselective formal synthesis of the polyketide marine natural product (-)-clavosolide A is presented. The construction of the beta-C-glycoside subunit is highlighted by a one-pot oxocarbenium cation formation/reduction sequence. Yamaguchi dimerization afforded the diolide aglycon in 18 steps (longest linear sequence).
Carrick
Jesse D
JD
Department of Chemistry, The University of Alabama, Tuscaloosa, Alabama 35487-0336, USA.
Jennings
Michael P
MP
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D001688:Biological Products; D018942:Macrolides; C455699:clavosolide A