title: Synthesis of the ABCDEF and FGHI ring system of yessotoxin and adriatoxin.
abstract: 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- and 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.
authors.affiliation: Department of Chemistry, University of Utah, Salt Lake City, UT, USA.
authors.forename: Yuan
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: Department of Chemistry, University of Utah, Salt Lake City, UT, USA.
authors.forename: Jon D
authors.initials: JD
authors.lastname: Rainier
mesh_terms: D000818:Animals; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D003500:Cyclization; D004141:Dinoflagellida / Q000378:metabolism; D015394:Molecular Structure; D008978:Mollusk Venoms; D035964:Oxocins / Q000138:chemical synthesis* / Q000737:chemistry; D049897:Pectinidae / Q000737:chemistry
chemical_list: D001688:Biological Products; D008978:Mollusk Venoms; D035964:Oxocins; C482966:adriatoxin; C066632:yessotoxin