Six-Step Syntheses of (-)-1-Deoxyaltronojirimycin and (+)-1-Deoxymannonojirimycin from N-Z-O-TBDPS-l-serinal

Meire Y Kawamura; Alexánder G Talero; João V Santiago; Edson Garambel-Vilca; Isac G Rosset; Antonio C B Burtoloso

doi:10.1021/acs.joc.6b01575

Six-Step Syntheses of (-)-1-Deoxyaltronojirimycin and (+)-1-Deoxymannonojirimycin from N-Z-O-TBDPS-l-serinal

J Org Chem. 2016 Nov 4;81(21):10569-10575. doi: 10.1021/acs.joc.6b01575. Epub 2016 Aug 19.

Authors

Meire Y Kawamura¹, Alexánder G Talero¹, João V Santiago¹, Edson Garambel-Vilca¹, Isac G Rosset¹, Antonio C B Burtoloso¹

Affiliation

¹ Instituto de Química de São Carlos, Universidade de São Paulo , CEP 13560-970, São Carlos, SP, Brazil.

PMID: 27501028
DOI: 10.1021/acs.joc.6b01575

Abstract

Highly stereoselective six-step syntheses of (-)-1-deoxyaltronojirimycin (altro-DNJ) and (+)-1-deoxymannojirimycin (manno-DNJ) from N-Cbz-O-TBDPS-l-serinal are described. Key transformations involve a two-step preparation of a functionalized dihydropyridin-3-one as a common intermediate followed by Luche reduction and dihydroxylation (for altro-DNJ). The same sequence employing an epoxidation/epoxide opening in place of dihydroxylation furnishes manno-DNJ.

Publication types

Research Support, Non-U.S. Gov't