Latrunculins: NMR study, two new toxins and a synthetic approach

Article abstract of DOI:10.1016/S0040-4020(01)96553-6

A complete ¹H and ¹³C NMR assignment of one of the latrunculins (B) was accomplished with the aid of 2D NMR COSY and CH shift-correlation experiments. The various H-H coupling constants have been determined and a conformation of the macrolide and the tetrahydropyran (THP) ring suggested on basis of the J-values and measured NOE's. The absolute configuration of latrunculin-A(1) was determined on the grounds of its earlier X-ray analysis, and a chemical degradation to a known compound. Two novel latrunculins, -C(3) and -D(4), were isolated from the Red Sea sponge L. magnifica and their structures elucidated. Starting with L-cysteine a synthon for the latrunculins has been synthesized.