Structure Identification: |
Tetrahedron Letters,2000,41(40): 7661-5. | Asymmetric total synthesis of natural pyrrolizidine alkaloid, (+)-alexine[Reference: WebLink] | METHODS AND RESULTS:
The total synthesis of the potent glycosidase inhibitor (+)-Alexine with five contiguous stereogenic centres [(1R,2R,3R,7S,7aS)-3-hydroxymethyl-1,2,7-trihydroxypyrrolizidine alkaloid] is described featuring the efficient and stereodefined novel elaboration of the functionalized homochiral lactam derived from 2,3,5-tri-O-benzyl-β-d-arabinofuranose. | Tetrahedron,2008,64(22):5254–5261. | New asymmetric strategy for the total synthesis of naturally occurring (+)-alexine and (−)-7-epi-alexine[Reference: WebLink] |
METHODS AND RESULTS:
(+)-Alexine [(1R,2R,3R,7S,7aS)-3-hydroxymethyl-1,2,7-trihydroxypyrrolizidine] and (−)-7-epi-Alexine [(1R,2R,3R,7R,7aS)-3-hydroxymethyl-1,2,7-trihydroxypyrrolizidine], as the potent glycosidase inhibitors by featuring the efficient and stereodefined elaboration of the functionalized pyrrolidine derivatives, which were, in turn, prepared via stereoselective manipulation of the homochiral allyl alcohol precursors derived from l-xylose. |
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