Synthesis of both possible isomers of the northwest quadrant of altromycin B.
The synthesis of the northwest quadrant of Altromycin B is described. The preparation of the two epimers at the quaternary carbon of the 6-deoxy-C-altrose moiety in the northwest quadrant is accomplished starting from d-glucose. A key step of our synthetic sequence is the formation of the C-glycoside linkage via the Ramberg-Bäcklund reaction. Two different routes are explored, which differ mainly on the timing of the conversion of glucose to altrose, either before or after the preparation of the C-glycoside. The conformation behavior of variously substituted C-altropyranoside rings is also discussed.
Pasetto
Paolo
P
Department of Chemistry, Hunter College of The City University of New York, 695 Park Avenue, New York, New York 10021, USA.
Franck
Richard W
RW
D000617:Aminoglycosides / Q000138:chemical synthesis* / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002236:Carbohydrate Conformation; D005947:Glucose / Q000737:chemistry; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
D000617:Aminoglycosides; D000970:Antineoplastic Agents; C063717:altromycin B; D005947:Glucose