A short synthesis of (2S,4S,5R)-4,5,6-trihydroxynorleucine
1994
Varela, O. | Nin, A.P. | De Lederkremer, R.M.
A direct synthesis of enantiomerically pure (2S,4S,5R)-4,5,6-trihydroxynorleucineb(1)from a carbohydrate precursor (D-glucosamine is described. D-glucosamine was oxidized to 2-amino 2-deoxy-D-gluconic acid (2), which was converted into the 2-acylamido-hex-2-enono-1,4-(3,4) and 1,5-lactone (5,6,11) derivatives. The hydrogenation of the enamine system of these compounds took place with exellent diastereofacial selectivity leading to the corresponding 3-deoxy-D-arabino-lactone derivatives (7-10,12,13,). On N-deacetylation with HCl the hydrochloride derivative of 1, in its 1,4-lactone form, was obtained with 57% overall yield, from 2. The ammonium salt of 1 was also prepared.
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