Total synthesis of siphonarin B and dihydrosiphonarin B |
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Authors: | Paterson Ian Chen David Yu-Kai Franklin Alison S |
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Institution: | University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, UK. ip100@cus.cam.ac.uk |
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Abstract: | The spirocyclic core of the siphonarins was constructed by a directed cyclization of a linear triketone, prepared using a Sn(II)-mediated aldol coupling and Swern oxidation at C9 and C13. To circumvent a facile retro-Claisen pathway generating a baconipyrone-type ester, a Ni(II)/ Cr(II)-mediated coupling reaction with vinyl iodide was used to complete the first synthesis of siphonarin B and dihydrosiphonarin B. A stable isomeric spiroacetal was also prepared which could not be equilibrated to the siphonarin skeleton. |
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