Antineoplastic agents. 450. Synthesis of (+)-pancratistatin from (+)-narciclasine as relay(1a).
(+)-Narciclasine (2) available in quantity from certain Amaryllidaceae species or by total synthesis was employed as a precursor for a 10-step synthetic conversion (3.6% overall yield) to natural (+)-pancratistatin (1a). The key procedures involved epoxidation of natural (+)-narciclasine (2) to epoxide 6, reduction to diol 8, and formation of cyclic sulfate 12 and its ring opening with cesium benzoate followed by saponification of the benzoate to afford (+)-pancratistatin (1a).
Pettit
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GR
Cancer Research Institute and Department of Chemistry and Biochemistry, Arizona State University, Tempe, AZ 85287-2404, USA.
Melody
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N
Herald
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DL
D000470:Alkaloids / Q000737:chemistry; D047151:Amaryllidaceae Alkaloids; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis*; D007546:Isoquinolines / Q000138:chemical synthesis*; D010617:Phenanthridines; D010946:Plants, Medicinal / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D047151:Amaryllidaceae Alkaloids; D000972:Antineoplastic Agents, Phytogenic; D007546:Isoquinolines; D010617:Phenanthridines; C010753:narciclasine; C044997:pancratistatin