Synthesis of carbasugars from aldonolactones. Part II. Preparation of polyhydroxy/aminocyclopentanes functionalised at all five ring carbons

Authors
Johansen, SK Lundt, I
Citation
Sk. Johansen et I. Lundt, Synthesis of carbasugars from aldonolactones. Part II. Preparation of polyhydroxy/aminocyclopentanes functionalised at all five ring carbons, J CHEM S P1, (24), 1999, pp. 3615-3622
Citations number
22
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
0300922X → ACNP
Issue
24
Year of publication
1999
Pages
3615 - 3622
Database
ISI
SICI code
0300-922X(1999):24<3615:SOCFAP>2.0.ZU;2-D
Abstract
Starting from (1R,5R,8 R)-8-acetoxy-2-oxabicyclo[3.3.0]oct-6-en-3-one 4 the syntheses of 5-deoxy-4a(R)-hydroxy-4a-carba-alpha-D-ribo-hexofuranose 17, 5-deoxy-4a(R)-hydroxy-4a-carba-alpha-D-lyxo-hexofuranose 21, 5-deoxy-4a(R)- hydroxy-4a-carba-alpha-D-xylo-hexofuranose 23 and 4a(R)-hydroxy-2-amino-2,5 -dideoxy-4a(R)-hydroxy-4a-carba-alpha-D-arabino-hexofuranose 1 have been ac hieved. The methodology included OsO4-catalysed dihydroxylation as well as regioselective epoxide opening followed by calcium borohydride reduction of the lactone moiety.