A short synthesis of (2S,4S,5R)-4,5,6-trihydroxynorleucine

Add time:07/24/2019    Source:sciencedirect.com

A direct synthesis of enantiomerically pure (2S,4S,5R)-4,5,6-trihydroxynorleucine (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 excellent 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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