Process for the preparation of castanospermine

Details Process for the preparation of castanospermine Process for the preparation of castanospermine

1990-03-12

1991-11-19

Berch, Mark L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548526, 549299, 549433, 549435, C07D47104, C07D49314, C07D49304

Patent

active

050668072

ABSTRACT:
Castanospermine is prepared by starting from 5-(t-BOC)amino-5-deoxy-1,2-O-isopropylidene-.alpha.-D-glucuronolactone. Two additional carbons are added to the starting material using ethyl acetate and a strong base and the resulting cyclic hemiketal is subjected to a series of reductions, with intervening removal of protecting groups, to give the castanospermine. A substituted hydroxypyrrolidinone and a substituted hydroxypyrrolidine serve as intermediates in the process.

REFERENCES:
Bashyal et al., Tetrahedron, 43, 415 (1987).
Bernotas et al., Tetrahedron Letters, 25, 165 (1984).
Setoi et al., Tetrahedron Letters, 26, 4617 (1985).
Hamana et al., J. Org. Chem., 52, 5492 (1987).
Reymond et al., Tetrahedron Letters, 30, 705 (1989).

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