A convergent total synthesis of hemibrevetoxin B.
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.
Zakarian
Armen
A
Department Of Chemistry, Florida State University, Tallahassee, FL 32306, USA.
Batch
Alexandre
A
Holton
Robert A
RA
D000818:Animals; D003500:Cyclization; D004141:Dinoflagellida / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D008387:Marine Toxins / Q000138:chemical synthesis*
D006576:Heterocyclic Compounds, 4 or More Rings; D008387:Marine Toxins; C409729:hemibrevetoxin B