BETA-OXY-ALPHA-DIAZO CARBONYL-COMPOUNDS .3. RH-2(ACO)(4) MEDIATED DECOMPOSITION OF BETA-ACETOXY-ALPHA-DIAZO ESTERS - APPLICATION TO THE SYNTHESIS OF NATURAL 3-DEOXY-2-KETO ALDONIC ACIDS (KDO AND DAH)

Authors
LOPEZHERRERA FJ SARABIAGARCIA F
Citation
Fj. Lopezherrera et F. Sarabiagarcia, BETA-OXY-ALPHA-DIAZO CARBONYL-COMPOUNDS .3. RH-2(ACO)(4) MEDIATED DECOMPOSITION OF BETA-ACETOXY-ALPHA-DIAZO ESTERS - APPLICATION TO THE SYNTHESIS OF NATURAL 3-DEOXY-2-KETO ALDONIC ACIDS (KDO AND DAH), Tetrahedron letters, 35(36), 1994, pp. 6705-6708
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
36
Year of publication
1994
Pages
6705 - 6708
Database
ISI
SICI code
0040-4039(1994)35:36<6705:BC.RMD>2.0.ZU;2-N
Abstract
beta-Acetoxy-alpha-diazo esters yield alpha-enol acetate esters quanti tatively by reaction with dirhodium tetraacetate. The reaction was use d to prepare the major natural compounds 3-Deoxy-D-arabino-2-Heptuloso nic acid (DAH, 1) and 3-Deoxy-D-manno-2-Octulosonic acid (KDO, 2) by c onversion of the enol acetate function to the corresponding ketone.