Synthesis of an F-H gambierol subunit using a C-glycoside-centered strategy.
[structure: see text] This manuscript describes our synthesis of the F-H subunit of gambierol. In addition to the synthesis of the tricycle, of note is an interesting protecting group influence on the generation of a C(23) C-glycoside as well as the use of ring-closing metathesis to generate a tetrasubstituted enol ether.
Majumder
Utpal
U
Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112, USA.
Cox
Jason M
JM
Rainier
Jon D
JD
D000818:Animals; D002922:Ciguatoxins; D003500:Cyclization; D004141:Dinoflagellida / Q000737:chemistry*; D004988:Ethers, Cyclic / Q000138:chemical synthesis*; D006027:Glycosides / Q000737:chemistry*; D007202:Indicators and Reagents; D010084:Oxidation-Reduction; D011083:Polycyclic Compounds / Q000138:chemical synthesis*; D035964:Oxocins
D002922:Ciguatoxins; D004988:Ethers, Cyclic; D006027:Glycosides; D007202:Indicators and Reagents; D011083:Polycyclic Compounds; C435770:gambierol; D035964:Oxocins