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Total synthesis of (±)-cycloclavine and (±)-5-epi-cycloclavine.

ABSTRACT: Novel routes to the naturally occurring indole alkaloid cycloclavine and its unnatural C(5)-epimer are described. Key features include the rapid construction of the heterocyclic core segments by two Diels-Alder reactions. An indole annulation was accomplished by a late-stage intramolecular Diels-Alder furan cycloaddition, and a methylenecyclopropane dienophile was used for a stereoselective intramolecular [4 + 2] cycloaddition to give the cyclopropa[c]indoline building block present in cycloclavine.

SUBMITTER: Petronijevic FR

PROVIDER: S-EPMC3111057 | biostudies-literature | 2011 May

REPOSITORIES: biostudies-literature

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Total synthesis of (±)-cycloclavine and (±)-5-epi-cycloclavine.

Petronijevic Filip R FR Wipf Peter P

Journal of the American Chemical Society 20110428 20

Novel routes to the naturally occurring indole alkaloid cycloclavine and its unnatural C(5)-epimer are described. Key features include the rapid construction of the heterocyclic core segments by two Diels-Alder reactions. An indole annulation was accomplished by a late-stage intramolecular Diels-Alder furan cycloaddition, and a methylenecyclopropane dienophile was used for a stereoselective intramolecular [4 + 2] cycloaddition to give the cyclopropa[c]indoline building block present in cycloclav ...[more]

PMID: 21517102

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