Antineoplastic agents. 450. Synthesis of (+)-pancratistatin from (+)-narciclasine as relay

Authors
Pettit, GR Melody, N Herald, DL
Citation
Gr. Pettit et al., Antineoplastic agents. 450. Synthesis of (+)-pancratistatin from (+)-narciclasine as relay, J ORG CHEM, 66(8), 2001, pp. 2583-2587
Citations number
31
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
66
Issue
8
Year of publication
2001
Pages
2583 - 2587
Database
ISI
SICI code
0022-3263(20010420)66:8<2583:AA4SO(>2.0.ZU;2-1
Abstract
(+)-Narciclasine (2) available in quantity from certain Amaryllidaceae spec ies or by total synthesis was employed as a precursor for a 10-step synthet ic conversion (3.6% overall yield) to natural (+)-pancratistatin (la). The key procedures involved epoxidation of natural (+)-narciclasine (2) to epox ide 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).