THE BIOMIMETIC SYNTHESIS OF TRANS-(1β-H,5α-H)-GUAIANOLIDES

Article abstract of DOI:10.1016/S0040-4020(01)86160-3

1-epigallicin 11 underwent biomimetic cyclization to trans-(1β-H,5α-H)-guaianolide 22, the stereoespecificity of this cyclization being credited to the fact that it took place via the reacting TC conformation 27.The epimeric nor-guaianolides 15 and 17 were prepared and their rearrangements studied.The biogenetic implications of these processes are discussed.