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

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.

SUBMITTER: Robles O

PROVIDER: S-EPMC5546918 | biostudies-literature | 2012 Mar

REPOSITORIES: biostudies-literature

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

Robles Omar O Serna-Saldívar Sergio O SO Gutiérrez-Uribe Janet A JA Romo Daniel D

Organic letters 20120224 6

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 ...[more]

PMID: 22360738

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