Facile ring transformation from gluconolactone to cyclitol derivative via spiro sugar ortho ester

Authors
Ohtake, H Ikegami, S
Citation
H. Ohtake et S. Ikegami, Facile ring transformation from gluconolactone to cyclitol derivative via spiro sugar ortho ester, ORG LETT, 2(4), 2000, pp. 457-460
Citations number
47
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
4
Year of publication
2000
Pages
457 - 460
Database
ISI
SICI code
1523-7060(20000224)2:4<457:FRTFGT>2.0.ZU;2-A
Abstract
[GRAPHICS] A short step preparation of cyclitol derivative 8 which is a versatile synt hon for the synthesis of valiolamine and its related compounds is described . Key steps in this preparation are a novel enol ether formation from spiro sugar ortho esters with AIMe(3) and an intramolecular Aldol condensation o f alkyl enol ethers catalyzed by ZnCl2 in THF-H2O. With these reactions, gl uconolactone derivative 1 was efficiently converted into 8 in short steps.