Total synthesis, structure revision, and absolute configuration of (+)-yatakemycin.

Total synthesis, structure revision, and absolute configuration of (+)-yatakemycin. Research Abstract Details 

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Total synthesis, structure revision, and absolute configuration of (+)-yatakemycin. Abstract Text:

Mark S Tichenor,David B Kastrinsky,Dale L Boger,

The total synthesis of the reported structure 2 for yatakemycin, an exceptionally potent, naturally occurring antitumor agent disclosed in 2003, and its lack of correlation with the natural product are detailed. On the basis of spectroscopic distinctions between 2 and yatakemycin, the natural product structure was reformulated as 3, now bearing a thiomethyl ester versus thioacetate in the left-hand subunit. Total synthesis of 3 provided a compound nearly identical to but still subtly distinct from the natural product. A second reformulation of the yatakemycin structure as 1, incorporating the alternatively substituted right-hand subunit as well as the initial thiomethyl ester reformulation, was confirmed by total synthesis of both (+)- and ent-(-)-1 in studies that also unambiguously established the absolute configuration of the natural product.

Total synthesis, structure revision, and absolute configuration of (+)-yatakemycin. Publishing Authors By Initials

MS Tichenor,DB Kastrinsky,DL Boger,

For similar bacteria: endospore-forming bacteria: gram-positive endospore-forming bacteria: gram-positive endospore-forming rods: streptomycetaceae: streptomyces research abstracts see: bacteria: endospore-forming bacteria: gram-positive endospore-forming bacteria: gram-positive endospore-forming rods: streptomycetaceae: streptomyces research

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Total synthesis, structure revision, and absolute configuration of (+)-yatakemycin. Journal Published:

PUBLICATION TYPE: Research Support, U.S. Gov't,

Journal: Journal of the American Chemical Society

VOLUME: 126

Page Numbers: 8396-8

Journal Abbreviation: J. Am. Chem. Soc.

ISSN: 0002-7863

DAY: 14

MONTH: Jul

YEAR: 2004

Total synthesis, structure revision, and absolute configuration of (+)-yatakemycin. Information

Number of References:

LANGUAGE: eng

NlmUniqueID: 7503056

Total synthesis, structure revision, and absolute configuration of (+)-yatakemycin. Keywords Mesh Terms:

KEYWORDS: Streptomyces

MESH TERMS: chemistry

Chemical & Substance for Abstract: Total synthesis, structure revision, and absolute configuration of (+)-yatakemycin. Information

Substance Name: yatakemycin

Registry Number: 0

Grant and Affiliation Information for Total synthesis, structure revision, and absolute configuration of (+)-yatakemycin.

AFFILIATION: Department of Chemistry and the Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.

Country: United States

AGENCY: United States NCI

GRANT: CA42056

ACRONYM: CA

MEDLINETA: J Am Chem Soc

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