D-glucosamine trimethylene dithioacetal derivatives: formation of six- and seven-membered ring amino carbasugars. Synthesis of (-)-calystegine B3.
By virtue of carefully chosen protecting groups, d-glucosamine trimethylene dithioacetal derivatives were successfully oxidized to the corresponding 6-aldehydes. This methodology reverses the donor and acceptor position on a normal open chain sugar and changes the relative position of the N-substituent. From the 6-aldehydes, heptose epoxide derivatives were prepared by a Corey-Chaykovsky reaction, and cyclized by the Corey-Seebach method. Depending on the designed protecting groups, the orthogonally protected six- and seven-membered ring amino carbasugars can be produced selectively and efficiently. (-)-Calystegine B(3) was synthesized from one of those products with high yield. This is the first anionic cyclization pathway to calystegine type structures.
Chen
Yue-Lei
YL
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, D-48149, Münster, Germany.
Redlich
Hartmut
H
Bergander
Klaus
K
Fröhlich
Roland
R
D002241:Carbohydrates / Q000138:chemical synthesis; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D009662:Nortropanes / Q000138:chemical synthesis*; D012991:Solanaceous Alkaloids / Q000138:chemical synthesis*
D002241:Carbohydrates; D009662:Nortropanes; D012991:Solanaceous Alkaloids; C095613:calystegine B(2); D005944:Glucosamine