Synthesis of the ABCDEF and FGHI ring system of yessotoxin and adriatoxin

Yessotoxin and adriatoxin are members of the polycyclic ether family of marine natural products. Outlined in this article is our synthetic approach to two subunits of these targets. Central to our strategy is a coupling sequence that employs an olefinic-ester cyclization reaction. As outlined, this sequence was used in two coupling sequences. First it was used to merge the A,B- and E,F-bicyclic precursors and in the process generate the C, D-rings. Second it was used to couple the F- and I-rings while building the eight-membered G-ring and subsequently the H-ring pyran.