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Org Lett. 2012 Mar 16;14(6):1394-7. doi: 10.1021/ol300105q. Epub 2012 Feb 24.

Cyclopropanations of olefin-containing natural products for simultaneous arming and structure activity studies.

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1
Department of Chemistry, Texas A&M University, P.O. Box 30012, College Station, Texas 77842-3012, United States.

Abstract

Cyclopropanations of alkene-containing natural products that proceed under mild conditions are reported for simultaneous arming and structure-activity relationship studies. An alkynyl diazo ester under Rh(II) catalysis is employed for cyclopropanations of electron-rich olefins while an alkynyl sulfonium ylide is used for electron-poor olefins. This approach enables simultaneous natural product derivatization for SAR studies and arming (i.e., via alkyne attachment) for subsequent conjugation with reporter tags (e.g., biotin, fluorophores, photoaffinity labels) for mechanism of action studies including cellular target identification and proteome profiling experiments.

PMID:
22360738
PMCID:
PMC5546918
DOI:
10.1021/ol300105q
[Indexed for MEDLINE]
Free PMC Article
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