Synthesis of caryophyllose. Use of n-BuLi/Na-O-t-Bu in the coupling of highly functionalized ketones and dithioacetals

Authors
Adinolfi, M Barone, G Festa, P Guariniello, L Iadonisi, A
Citation
M. Adinolfi et al., Synthesis of caryophyllose. Use of n-BuLi/Na-O-t-Bu in the coupling of highly functionalized ketones and dithioacetals, TETRAHEDR L, 41(25), 2000, pp. 4981-4985
Citations number
11
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
25
Year of publication
2000
Pages
4981 - 4985
Database
ISI
SICI code
0040-4039(20000619)41:25<4981:SOCUON>2.0.ZU;2-H
Abstract
The C-4 branched monosaccharide caryophyllose 2a was synthesized by a conve rgent approach relying on the coupling of metalated dithioacetal 4b with ke tone 3. Combined use of n-BuLi and t-Bu-ONa as deprotonation system for 4b turned out to be decisive for the success off this coupling. (C) 2000 Elsev ier Science Ltd. All rights reserved.