Abstract
(+)-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).
Publication types
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, Non-P.H.S.
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Alkaloids / chemistry
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Amaryllidaceae Alkaloids*
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Antineoplastic Agents, Phytogenic / chemical synthesis*
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Isoquinolines / chemical synthesis*
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Phenanthridines*
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Plants, Medicinal / chemistry
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Stereoisomerism
Substances
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Alkaloids
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Amaryllidaceae Alkaloids
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Antineoplastic Agents, Phytogenic
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Isoquinolines
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Phenanthridines
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narciclasine
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pancratistatin