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C-glycosides to fused polycyclic ethers. A formal synthesis of (+/-)-hemibrevetoxin B
J D Rainier1, S P Allwein, J M Cox
1Department of Chemistry, The University of Arizona, Tucson, Arizona 85721, USA. rainier@u.arizona.edu
The Journal of Organic Chemistry
|April 21, 2001
Abstract:
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.