Total synthesis of (-)-spirotryprostatin B: synthesis and related studies |
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Authors: | Marti Christiane Carreira Erick M |
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Institution: | Laboratorium für Organische Chemie der ETH-Zürich, HCI H 335, Wolfgang Pauli Strasse 10, CH-8093 Zurich, Switzerland. |
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Abstract: | The total synthesis of spirotryprostatin B, a cytostatic spiropyrrolidine-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 spirocyclopropane-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. |
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