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Total synthesis of (-)-spirotryprostatin B: synthesis and related studies.
Journal article

Total synthesis of (-)-spirotryprostatin B: synthesis and related studies.

  • Marti C Laboratorium für Organische Chemie der ETH-Zürich, HCI H 335, Wolfgang Pauli Strasse 10, CH-8093 Zurich, Switzerland.
  • Carreira EM
  • 2005-08-11
Published in:
  • Journal of the American Chemical Society. - 2005
Antineoplastic Agents
Molecular Structure
Piperazines
Spiro Compounds
English The total synthesis of spirotryprostatin B, a cytostatic spiro[pyrrolidine-3,3'-oxindole] alkaloid, is described. The key step of the synthetic approach consists of the application of the MgI2-mediated ring-expansion reaction of a spiro[cyclopropane-1,3'-oxindole] with an aldimine, leading to rapid assembly of the spirotryprostatin core. The route documents the installation of the prenyl side chain by Julia-Kocieński olefination of a key aldehyde precursor, a transformation that ultimately allows for facile synthesis of analogues and facilitates structure-activity relationships studies.
Language
  • English
Open access status
closed
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Persistent URL
https://folia.unifr.ch/global/documents/67159
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