Total Synthesis of Coraxeniolide-A

Abstract

The first total synthesis of optically active coraxeniolide-A (1a) and 4-epi-coraxeniolide-A (1b) is described. The approach is highly stereoselective and flexible in the preparation of a wide variety of members of the xeniolide family. The use of the Grob-fragmentation was pivotal for the stereospecific elaboration of the nine-membered ring. Coraxeniolide-A (1a) was synthesized in 28 steps by using the Hajos-Parrish diketone 2 as starting material which is available enantiomerically pure.