Stereochemical assignment of the C-1-C-6 fragment of psymberin by synthesis and natural product degradation

Psymberin is a sponge-derived natural product that shows striking selectivity as a cytotoxic agent. Conformational mobility has precluded stereochemical assignment for the acyl fragment of this molecule (psymberic acid) by NMR. Herein we report stereoselective syntheses of all four stereoisomers of...

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Bibliographic Details
Published inOrganic letters Vol. 7; no. 19; pp. 4117 - 4120
Main Authors Green, ME, Rech, JC, Floreancig, PE
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 15.09.2005
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
AGENTS
THEONELLA SP
STRUCTURE ELUCIDATION
MARINE SPONGE
PEDERIN FAMILY
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Summary:Psymberin is a sponge-derived natural product that shows striking selectivity as a cytotoxic agent. Conformational mobility has precluded stereochemical assignment for the acyl fragment of this molecule (psymberic acid) by NMR. Herein we report stereoselective syntheses of all four stereoisomers of psymberic acid. A comparison of the acid-mediated cyclization products of these compounds to the product of psymberin's acidic methanolysis showed the stereochemical configuration of this fragment to be 4S, 5S.
Bibliography:Medline
NIH RePORTER
ISSN:1523-7060
1523-7052
DOI:10.1021/ol051396s