Total synthesis and determination of relative and absolute configuration of multiplolide A.
A flexible approach for total syntheses of possible multiplolide A diastereomers establishing the relative and absolute configuration is documented. The adopted strategy features ring-closing metathesis (RCM) as the key reaction and screening of a set of substrates for the feasibility of RCM in general and for the requisite E-configuration of ring olefin in particular. Selective protecting groups manipulation prior to the assembly of the central macrocyclic core was instrumental in installing the epoxide functionality on a fully deprotected nonenolide at the end of the synthesis.
Ramana
C V
CV
National Chemical Laboratory, Pune, India. vr.chepuri@ncl.res.in
Khaladkar
Tushar P
TP
Chatterjee
Soumitra
S
Gurjar
Mukund K
MK
D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry*; D008968:Molecular Conformation; D013237:Stereoisomerism
D007783:Lactones; C435879:multiplolide A