title: C-glycosides to fused polycyclic ethers. A formal synthesis of (+/-)-hemibrevetoxin B.
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.
authors: Department of Chemistry, The University of Arizona, Tucson, Arizona 85721, USA. rainier@u.arizona.edu
authors: J D
authors: JD
authors: Rainier
authors: S P
authors: SP
authors: Allwein
authors: J M
authors: JM
authors: Cox
mesh_terms: D004987:Ethers / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D004987:Ethers; D006027:Glycosides; D006576:Heterocyclic Compounds, 4 or More Rings; C409729:hemibrevetoxin B