A convergent total synthesis of hemibrevetoxin B.
نویسندگان
چکیده
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.
منابع مشابه
C-glycosides to fused polycyclic ethers. A formal synthesis of (+/-)-hemibrevetoxin B.
This paper describes a formal total synthesis of the marine ladder toxin hemibrevetoxin B from Danishefsky's dienes. This approach couples the generation of C-glycosides from cyclic enol ethers with metathesis or acid-mediated annulation reactions. The result is a highly efficient synthesis of the tetracyclic ring system of hemibrevetoxin B.
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ورودعنوان ژورنال:
- Journal of the American Chemical Society
دوره 125 26 شماره
صفحات -
تاریخ انتشار 2003