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.
Rainier
J D
JD
Department of Chemistry, The University of Arizona, Tucson, Arizona 85721, USA. rainier@u.arizona.edu
Allwein
S P
SP
Cox
J M
JM
D004987:Ethers / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
D004987:Ethers; D006027:Glycosides; D006576:Heterocyclic Compounds, 4 or More Rings; C409729:hemibrevetoxin B