New convenient synthesis of tunicamine

✍ Scribed by Jan Ramza; Aleksander Zamojski

• Publisher: Elsevier Science
• Year: 1992
• Tongue: French
• Weight: 805 KB
• Volume: 48
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)89859-8

✦ Synopsis

A synthesis of tunicamine, the eleven-carbon atom sugar component of atnicamycin antibiotics, was described The synthesis started from a derivative of 2-azi&-2-deoxy-D-galactose (11) which was condensed with a firfuryl alcohol moiety. Achmatowicz-type transformation of this moiety to allofiranose system yielded a derivative of tunicamine. The synthesis required I1 steps and yielded 27 in

5.4% yield @om 11) and with good stereoselectivity.