In the last few decades there has been ample research reporting methods for introducing consecutive and multiple hydroxyl and amine functional groups into many valuable molecules. However, a more efficient general method is still needed with full control of the stereochemistry of all hydroxyl and amine functional groups. Among them, 1,3,4-trihydroxy-2-amine, with specific configurations as 2S, 3S and 4R, is often found in biologically important natural products, among them sphingolipids, calyculin fragment C33-C37 and several azasugar family. In this study we describe a stereoselective and straightforward synthesis of the common calyculin fragment C33-C37, (-)-1,4-dideoxy-1,4-imino-L-ribitol, (+)-1,4-dideoxy-1,4-imino-D-ribitol, hyacinthacine A1 and hyacinthacine A1 analogues from chiral aziridine.

Stereoselective synthesis of azasugars from chiral aziridine

248th National Meeting (2014)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.