Total Synthesis of Siphonarin B and Dihydrosiphonarin B

Total Synthesis of Siphonarin B and Dihydrosiphonarin B

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 cou...

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Veröffentlicht in:Organic letters 2002-02, Vol.4 (3), p.391-394
Hauptverfasser: Paterson, Ian, Chen, David Yu-Kai, Franklin, Alison S
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Sprache:eng
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Ketones - chemical synthesis
Molecular Structure
Spiro Compounds - chemical synthesis
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creator Paterson, Ian
Chen, David Yu-Kai
Franklin, Alison S
description 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.
doi_str_mv 10.1021/ol017082w
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subjects Ketones - chemical synthesis
Molecular Structure
Spiro Compounds - chemical synthesis
title Total Synthesis of Siphonarin B and Dihydrosiphonarin B
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