title: Total synthesis of brevetoxin-B.
abstract: Brevetoxin-B (BTX-B), produced by the red tide organism, Gymnodium breve Davis, is the first member of marine polycyclic ethers to be structurally elucidated and one of the most potent neurotoxins. The structural feature is a trans-fused polycyclic ether ring system with 23 stereocenters. Its unique, complex structure and potent biological activity have attracted the attention of synthetic organic chemists. Total synthesis of BTX-B has been accomplished via the coupling of the ABCDEFG and IJK-ring segments, each ether ring of which was stereoselectively and efficiently constructed on the basis of SmI2-induced intramolecular cyclization, 6-endo-cyclization of hydroxy epoxide, ring-closing olefin metathesis, and SmI2-induced intramolecular Reformatsky-type reaction. Several kinds of double reactions at the left and right sides were efficiently used through the synthesis.
authors.affiliation: RIKEN (The Institute of Physical and Chemical Research), Wako, Saitama 351-0198, Japan.
authors.forename: Goh
authors.initials: G
authors.lastname: Matsuo
authors.forename: Koji
authors.initials: K
authors.lastname: Kawamura
authors.forename: Nobuyuki
authors.initials: N
authors.lastname: Hori
authors.forename: Hiroko
authors.initials: H
authors.lastname: Matsukura
authors.forename: Tadashi
authors.initials: T
authors.lastname: Nakata
mesh_terms: D000818:Animals; D004141:Dinoflagellida / Q000737:chemistry; D008387:Marine Toxins / Q000138:chemical synthesis*; D035964:Oxocins / Q000138:chemical synthesis*; D000095702:Polyether Toxins
chemical_list: D008387:Marine Toxins; D035964:Oxocins; C043466:brevetoxin B; D000095702:Polyether Toxins