ChemInform Abstract: Stereocontrolled and Enantioselective Synthesis of the Branched 6-Amino-4,6-deoxyheptopyranuronic Acid Component of Amipurimycin.

✍ Scribed by P. GARNER; J. U. YOO; R. SARABU; V. O. KENNEDY; W. J. YOUNGS

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 42 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199846247

✦ Synopsis

Stereocontrolled and Enantioselective Synthesis of the Branched 6-Amino-4,6-deoxyheptopyranuronic Acid Component of Amipurimycin.

-Key steps in the title synthesis of diastereomeric peptides (XIV)/(XV) include the stereodivergent assembly of the dihydropyrone (III), elaboration of the tetrahydropyran ring to give acid ester (XII), and introduction of the cis cyclopentane moiety (XIII). The same reaction sequence is accomplished with (S)-(II) to give the C-6 epimers of (XIV)/(XV) in similar yields and stereoselectivities. -(GARNER, P.; YOO,