Synthesis of trans-fused tetrahydropyrans via intramolecular cyclization of alpha-bromo-gamma '-hydroxy ketones

Authors
Mori, Y Yaegashi, K Furukawa, H
Citation
Y. Mori et al., Synthesis of trans-fused tetrahydropyrans via intramolecular cyclization of alpha-bromo-gamma '-hydroxy ketones, TETRAHEDR L, 40(40), 1999, pp. 7239-7242
Citations number
14
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
40
Year of publication
1999
Pages
7239 - 7242
Database
ISI
SICI code
0040-4039(19991001)40:40<7239:SOTTVI>2.0.ZU;2-A
Abstract
A practical method for the synthesis of trans-fused polytetrahydropyrans us ing racemic cis- and trans-epoxy sulfones was developed. Four diastereoisom ers, obtained by the reaction of an optically active triflate and the oxira nyl anions generated from racemic cis- and trans-epoxy sulfones, were trans formed into alpha-bromo-gamma'-hydroxy ketones, and the DBU-induced intramo lecular cyclization gave tetrahydropyranones. (C) 1999 Elsevier Science Ltd . All rights reserved.