Total synthesis of (-)-spirotryprostatin B: synthesis and related studies.
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.
Marti
Christiane
C
Laboratorium für Organische Chemie der ETH-Zürich, HCI H 335, Wolfgang Pauli Strasse 10, CH-8093 Zurich, Switzerland.
Carreira
Erick M
EM
D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D015394:Molecular Structure; D010879:Piperazines / Q000138:chemical synthesis*; D013141:Spiro Compounds / Q000138:chemical synthesis*
D000970:Antineoplastic Agents; D010879:Piperazines; D013141:Spiro Compounds; C101781:spirotryprostatin B