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).
Original language | English (US) |
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Pages (from-to) | 2583-2587 |
Number of pages | 5 |
Journal | Journal of Organic Chemistry |
Volume | 66 |
Issue number | 8 |
DOIs | |
State | Published - Apr 20 2001 |
ASJC Scopus subject areas
- Organic Chemistry