Regiochemical control in the synthesis of tetrahydrofurans by acid-catalyzed cyclization of hydroxy selenides and hydroxy sulfides

Authors
Gruttadauria, M Lo Meo, P Noto, R
Citation
M. Gruttadauria et al., Regiochemical control in the synthesis of tetrahydrofurans by acid-catalyzed cyclization of hydroxy selenides and hydroxy sulfides, TETRAHEDRON, 55(15), 1999, pp. 4769-4782
Citations number
23
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
15
Year of publication
1999
Pages
4769 - 4782
Database
ISI
SICI code
0040-4020(19990409)55:15<4769:RCITSO>2.0.ZU;2-W
Abstract
An efficient regiochemical control in the synthesis of tetrahydrofurans was achieved by acid-catalyzed cyclization of hydroxy-selenides (10a) and (11a ) which cyclize in the endo/exo mode and by hydroxy-sulfides (10c) and (11c ) which cyclize in the exo mode. By cyclization of the relevant hydroxy-sel enides, the C15-C20 fragment of (+)-Rolliniastatin 1 was obtained. Semiempi rical calculations (PM3) were used in rationalizing experimental results. ( C) 1999 Elsevier Science Ltd. All rights reserved.