Synthesis of medium and large rings, XLVII Synthesis of heptano bridged pyranoside derivatives

Authors
Kirsch, V Wolff, C Nather, C Tochtermann, W
Citation
V. Kirsch et al., Synthesis of medium and large rings, XLVII Synthesis of heptano bridged pyranoside derivatives, EUR J ORG C, (9), 2000, pp. 1741-1744
Citations number
15
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
9
Year of publication
2000
Pages
1741 - 1744
Database
ISI
SICI code
1434-193X(200005):9<1741:SOMALR>2.0.ZU;2-5
Abstract
Addition of dichlorocarbene to the glycal (+/-)-2 followed by cyclopropyl-a llyl rearrangement leads to the chloro-2H-pyran (+/-)-4. Oxidation of (+/-) -4 and reduction of the obtained hydroxypyranone (+/-)-5 gave the methyl py ranoside (+/-)-6. The relative configuration of (+/-)-6 was established by X-ray structural analysis of the corresponding acetate (+/-)-7. The synthes is of the optically active starting materials (+)-2 and (-)-2 is also repor ted.