Synthetic studies on spongistatins: synthesis of the C29-C44 fragment

Authors
Samadi, M Munoz-Letelier, C Poigny, S Guyot, M
Citation
M. Samadi et al., Synthetic studies on spongistatins: synthesis of the C29-C44 fragment, TETRAHEDR L, 41(18), 2000, pp. 3349-3353
Citations number
37
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
18
Year of publication
2000
Pages
3349 - 3353
Database
ISI
SICI code
0040-4039(20000429)41:18<3349:SSOSSO>2.0.ZU;2-2
Abstract
A convergent synthesis of the C29-C44 fragment, the common subunit of the s pongipyran macrolides is described. The key step of the synthesis is the C- glycosidation reaction which is based on coupling of the lithiated F-ring s ulfone with the E-ring aldehyde, and subsequent reductive desulfonylation t o afford the E-F bis (pyran) with high stereoselectivity at the anomeric ca rbon. (C) 2000 Elsevier Science Ltd. All rights reserved.