title: A convergent total synthesis of hemibrevetoxin B.
abstract: A convergent biomimetic synthesis of hemibrevetoxin B from d-glucal and d-arabinose utilizes an electrophile-promoted cascade anti-Baldwin cyclization of an epoxy alcohol. The epoxy alcohol arises from a palladium-catalyzed coupling of a highly functionalized organozinc compound and an alkenyl iodide, which serve as two chiral building blocks of similar size and complexity. This first successful implementation of a cascade epoxy alcohol cyclization for the synthesis of marine polycyclic ether toxins proceeds in 39 steps and 4% overall yield.
authors.affiliation: Department Of Chemistry, Florida State University, Tallahassee, FL 32306, USA.
authors.forename: Armen
authors.initials: A
authors.lastname: Zakarian
authors.forename: Alexandre
authors.initials: A
authors.lastname: Batch
authors.forename: Robert A
authors.initials: RA
authors.lastname: Holton
mesh_terms: D000818:Animals; D003500:Cyclization; D004141:Dinoflagellida / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D008387:Marine Toxins / Q000138:chemical synthesis*
chemical_list: D006576:Heterocyclic Compounds, 4 or More Rings; D008387:Marine Toxins; C409729:hemibrevetoxin B