Asymmetric Total Synthesis and Stereochemical Revision of Gymnangiamide

The asymmetric total synthesis of the originally proposed structure of gymnangiamide, a cytotoxic pentapeptide isolated from the marine hydroid Gymnangium regae Jaderholm, has been achieved. Key to the synthesis was the use of asymmetric hydrogenation of α-substituted β-ketoesters through dynamic ki...

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Published inOrganic letters Vol. 11; no. 9; pp. 1995 - 1997
Main Authors Tone, Hitoshi, Buchotte, Marie, Mordant, Céline, Guittet, Eric, Ayad, Tahar, Ratovelomanana-Vidal, Virginie
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.05.2009
Amer Chemical Soc
Subjects
Animals
Cellular Biology
Chemistry
Chemistry, Organic
Hydra
Hydra - chemistry
Life Sciences
Marine Biology
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Oligopeptides
Oligopeptides - chemical synthesis
Oligopeptides - chemistry
Oligopeptides - pharmacology
Physical Sciences
Science & Technology
Stereoisomerism
RUTHENIUM-CATALYZED HYDROGENATION
RU-SYNPHOS(R)
DYNAMIC KINETIC RESOLUTION
ESTERS
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Summary:The asymmetric total synthesis of the originally proposed structure of gymnangiamide, a cytotoxic pentapeptide isolated from the marine hydroid Gymnangium regae Jaderholm, has been achieved. Key to the synthesis was the use of asymmetric hydrogenation of α-substituted β-ketoesters through dynamic kinetic resolution for the preparation of nonproteinogenic chiral amino acids. The disparity of the NMR spectra between the synthetic material containing the l-serine residue and the natural product required a revision of the proposed structure.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol900184d