A concise and stereoselective synthesis of the A-ring fragment of the gambieric acids.
The A-ring fragment of the gambieric acids has been prepared by a short and efficient route. The key 3(2H)-furanone intermediate has been obtained by [2,3] rearrangement of an allylic oxonium ylide generated from intramolecular reaction of a crotyl ether with a copper carbenoid. A single stereogenic center has been set by using a chiral pool starting material and the other three have been established by using highly diastereoselective substrate-controlled transformations. [reaction--see text]
Clark
J Stephen
JS
School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, United Kingdom. j.s.clark@nottingham.ac.uk
Fessard
Thomas C
TC
Wilson
Claire
C
D002922:Ciguatoxins / Q000138:chemical synthesis* / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
D004988:Ethers, Cyclic; D002922:Ciguatoxins; C080898:gambieric acid A