CONVERGENT SYNTHESIS OF POLYETHER IONOPHORE ANTIBIOTICS - PROTECTIVE MANIPULATION AND SYNTHESIS OF MONENSIN-A

Authors
IRELAND RE MEISSNER RS RIZZACASA MA
Citation
Re. Ireland et al., CONVERGENT SYNTHESIS OF POLYETHER IONOPHORE ANTIBIOTICS - PROTECTIVE MANIPULATION AND SYNTHESIS OF MONENSIN-A, Journal of the American Chemical Society, 115(16), 1993, pp. 7166-7172
Citations number
19
Categorie Soggetti
Chemistry
Journal title
Journal of the American Chemical Society → ACNP
ISSN journal
00027863
Volume
115
Issue
16
Year of publication
1993
Pages
7166 - 7172
Database
ISI
SICI code
0002-7863(1993)115:16<7166:CSOPIA>2.0.ZU;2-S
Abstract
The protective manipulation and synthesis of the polyether antibiotic monensin is described. The hydroxyl groups and the carboxylic acid of monensin are protected, and its spiroketal is equilibrated to provide naturally derived, advanced targets for comparison to the synthetic ma terials. The total synthesis of these targets from spiroketal acids 3a x and 3eq and tricyclic glycal 4 by a highly convergent ester enolate Claisen rearrangement is described. Finally, the deprotection of each to monensin is described.