Studies toward the total synthesis of sorangiolides and their analogues. A convergent stereoselective synthesis of the macrocyclic lactone precursors.
Stereoselective synthesis of the fully protected 18-membered macrocyclic lactones as the immediate precursors of the natural products, sorangiolides A and B, is described. The key steps used in the synthesis include the sp3-hybridized carbon-carbon Fu cross coupling, the stereoselective Evans' aldol reaction with 1,5-anti induction, the 1,3-diastereoselective syn reduction of a beta-hydroxyketone intermediate, and Mukaiyama macrolactonization reactions.
Das
Sanjib
S
The Skaggs Institute for Chemical Biology and the Department of Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Abraham
Sunny
S
Sinha
Subhash C
SC
D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D007850:Lauric Acids / Q000138:chemical synthesis / Q000737:chemistry; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D007783:Lactones; D007850:Lauric Acids; D047028:Macrocyclic Compounds; C096605:sorangiolid A; C521909:sorangiolide B