The total synthesis and structural revision of stagonolide D.
The total synthesis of the putative structure of stagonolide D has been completed. The relative and absolute configuration of stagonolide D was established by synthesizing its optical antipode. The adopted strategy involves the construction of the central macrolide employing ring-closing metathesis (RCM), followed by selective protecting group manipulations and a final concomitant -OTBS deprotection and displacement of an -OMs placed next to it, resulting in the formation of the epoxide ring.
National Chemical Laboratory (CSIR-NCL), Dr. Homi Bhabha Road, Pune-411 008, India.
Paresh M
PM
Vadhadiya
Vedavati G
VG
Puranik
C V
CV
Ramana
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D001643:Bridged Bicyclo Compounds; D007783:Lactones; C572694:stagonolide D