Intermediates in a process for the preparation of castanospermin

Details Intermediates in a process for the preparation of castanospermin Intermediates in a process for the preparation of castanospermin

1991-06-10

1992-03-03

Lee, Mary C.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549299, 549433, 549435, C07D40504, C07D30792, C07D31770

Patent

active

050935011

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:
CA 108:6355q, The Synthesis of polyhydroxylated . . . dihydroxyproline, Bashyal et al., Tetrahedron (1987).
CA 113:97939a, Efficient synthesis . . . deoxynojirimycin, Anzeveno et al., Tetrahedron Letter (1990).
CA 114:164582q, An efficient, . . . castanospermine, Anzeveno et al., Tetrahedron Letter (1990).

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