American Chemical Society
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C-Glycosides to Fused Polycyclic Ethers. A Formal Synthesis of (±)-Hemibrevetoxin B

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journal contribution
posted on 2001-01-25, 00:00 authored by Jon D. Rainier, Shawn P. Allwein, Jason M. Cox
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.