doi: 10.1021/ol049483s.
A concise and stereoselective synthesis of the A-ring fragment of the gambieric acids
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- PMID: 15151411
- DOI: 10.1021/ol049483s
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A concise and stereoselective synthesis of the A-ring fragment of the gambieric acids
Org Lett.
.
Abstract
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]
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