Synthesis of (-) swainsonine and intermediate compounds employed

Details Synthesis of (-) swainsonine and intermediate compounds employed Synthesis of (-) swainsonine and intermediate compounds employed

1991-08-14

1993-02-16

Berch, Mark L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548565, 548453, 549454, 558 52, 560183, C07D48704, C07D491056, C07D31730

Patent

active

051872790

ABSTRACT:
(-)-Swainsonine is prepared by the steps of first reacting a compound having the formula: ##STR1## wherein each R.sub.2 is lower alkyl, with (4-carbalkoxybutyl) triphenylphosphonium bromide in a strong base to obtain an alcohol having the formula: ##STR2## wherein R.sub.2 is as defined above and R is C.sub.1 -C.sub.8 alkyl; the alcohol is then reacted with methanesulfonyl chloride or p-toluenesulfonyl chloride or benzenesulfonyl chloride in the presence of a tertiary amine to obtain the corresponding sulfonate. Heating the sulfonate with an azide in an organic solvent yields an imine having the formula: ##STR3## wherein R.sub.2 and R are ad defined above. Treating the imine with an inorganic base, in aqueous alcohol provides upon acidification, the corresponding acid. Heating the acid at reflux temperature in organic solvent, yields an enamide having the formula: ##STR4## wherein R.sub.2 is as defined above. Treating the enamide with diborane followed by reaction with hydrogen peroxide provides a protected swainsonine having the formula: ##STR5## which upon acid hydrolysis gives swainsonine.

REFERENCES:
Hajek, Chem Abs 78, 136086a (1973).
Bennett, J. Amer. Chem Soc III 2580 (1989).

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