%0 Journal Article %J European Journal of Organic Chemistry %D 2016 %T Enantioselective modular total synthesis of macrolides Sch725674 and C-4-epi-Sch725674 %A Sharma, Brijesh M. %A Gontala, Arjun %A Kumar, Pradeep %K Asymmetric synthesis %K Hydrolytic kinetic resolution %K Macrocycles %K Metathesis %K Natural products %X

The convergent total synthesis of Sch725674 has been accomplished by starting from (R)-1,2-epoxyheptane and assembling five modules in a highly stereoselective manner to give the final product in 6.6% overall yield. The same strategy was extended to the synthesis of its C-4 epimer. Key reactions of the synthetic pathway include a Jacobsen hydrolytic kinetic resolution of an epoxide followed by its regioselective opening through a Yamaguchi-Hirao alkynylation, and ring-closing metathesis reaction to furnish the unique 14-membered ring macrolactone. In addition, the influence of protecting groups on the efficiency of the ring-closing metathesis (RCM) macrocyclization has been studied to maximize its yields.

%B European Journal of Organic Chemistry %I WILEY-V C H VERLAG GMBH %C POSTFACH 101161, 69451 WEINHEIM, GERMANY %P 1215-1226 %8 FEB %G eng %N 6 %3

Foreign

%4 3.068 %R 10.1002/ejoc.201501531