A Convergent Total Synthesis of Hemibrevetoxin B
2003; American Chemical Society; Volume: 125; Issue: 26 Linguagem: Inglês
10.1021/ja029225v
ISSN1943-2984
AutoresArmen Zakarian, Alexandre Batch, Robert A. Holton,
Tópico(s)Carbohydrate Chemistry and Synthesis
ResumoA 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.
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