Synthesis of swainsonine and analogs thereof

Details Synthesis of swainsonine and analogs thereof Synthesis of swainsonine and analogs thereof

1991-01-23

1991-12-24

Springer, David B.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546112, C07D47100, C07D47104

Patent

active

050754572

ABSTRACT:
Swainsonine and analogs, namely 1,4-dideoxy-1,4-imino-D-mannitol and the novel ring contracted swainsonines, .DELTA.(1S,2R,7R,7aR)-1,2-trihydroxypyrrolizidine and (1S,2R,7S,7aR)-1,2,7-trihydroxypyrrolizidine, are synthesized from the divergent intermediate, 4,5-anhydro-1-azido-1-deoxy-2,3-O-isopropylidene-D-talitol. These novel compounds are glycosidase inhibitors.

REFERENCES:
Fleet et al., J. Chem. Soc. Chem. Commun. 1240-1241 (1984).
Cenci di Bello et al., Biochem. J. 259, 855-861 (1989).
Al Daher et al., Biochem. J. 258, 613-615 (1989).
Bashyal et al., Tetrahedron 43, 3083-3093 (1987).
Dener et al., J. Org. Chem. 53, 6022 (1988).
Bennett et al., J. Am. Chem. Soc. 111, 2580 (1989).
Fleet et al., Tetrahedron 44, 2649-2655 (1988).
Setoi et al., J. Org. Chem. 50, 3948 (1985).

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