Polyhydroxy Amino Acid Derivatives via β-Lactams Using Enantiospecific Approaches and Microwave Techniques

• Published in: Tetrahedron Vol. 56; no. 31; pp. 5603 - 5619
• Main Authors: Bose, Ajay K, Banik, Bimal K, Mathur, Chandra, Wagle, Dilip R, Manhas, Maghar S
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 28.07.2000; Elsevier
• Subjects: amino acids; amino sugars; annulation; azetidinones; Chemistry; Chemistry, Organic; enantiospecific; microwave irradiation; Physical Sciences; Science & Technology; amino sugars; microwave irradiation; annulation; enantiospecific; azetidinones; amino acids; CONVENIENT SYNTHESIS; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; D-GLYCERALDEHYDE; L-(S)-GLYCERALDEHYDE ACETONIDE; STEREOSELECTIVE SYNTHESIS; ORGANIC-REACTION ENHANCEMENT; 5-O-CARBAMOYLPOLYOXAMIC ACID; (+)-POLYOXAMIC ACID; POLYOXAMIC ACID
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/S0040-4020(00)00410-5

Enantiospecific synthesis has been developed for α-hydroxy β-lactams of predictable absolute configuration starting with readily available carbohydrates. Stereospecific approaches and microwave assisted chemical reactions have been utilized for the preparation of these 3-hydroxy-2-azetidinones and their conversion to natural or non-natural enantiomeric forms of intermediates for gentosamine, 6-epi-lincosamine, γ-hydroxythreonine, and polyoxamic acid.