FIRST SYNTHESIS OF THE DIFURANSESQUITERPENE ATHANASIN AND THE ELUCIDATION OF ITS RELATIVE AND ABSOLUTE CONFIGURATION

Article abstract of DOI:10.1016/S0040-4020(01)96205-2

The synthesis of the naturally occurring difuransesquiterpene athanasin is described.Employing Seebach's method of "self-reproduction of chirality", the chiral oxirane 6 is built up, which is successively connected with suitable furan building blocks.Cyclization of the resulting diols 14a/b gives the enantiomerically pure diastereomers 1a and 1b.Comparison of their spectroscopic data with athanasin after separation allows the elucidation of the natural product's relative and absolute configuration. Key Words: Difuransesquiterpene; natural product synthesis; special furan building blocks; relative and absolute configuration; optical rotations