Contribution to the synthesis of polyhydroxylated indolizidines starting from sugar isothiocyanates.

A straightforward stereoselective route towards castanospermine analogues starting from the corresponding d - gluco - and l - ido -hexofuranose isothiocyanates (5 S )- 2 and (5 R )- 2 is described. The key transformations of this approach rely on ring-closing metathesis and reductive amination to form the final polyhydroxylated indolizidines 10 – 13 in good overall yields. [ABSTRACT FROM AUTHOR]