• Bulletin of the Korean Chemical Society
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• v.30 no.7
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• pp.1531-1534
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• 2009

(2S,3R)-3-Hydroxy-2-(hydroxymethyl)-3,6-dihydro-2H-pyridine 8, an important precursor for the synthesis of polyhydroxylated piperidine azasugars, has been prepared from L-serine. Highly stereoselective nucleophilic addition to amino aldehyde 5 gave the corresponding allylic alcohol 6 which proceeded to give dihydro-2H-piridine 7a via a Grubbs II catalyzed RCM. Stereoselective H-bond directed epoxidation of allylic alcohol led to the oxiranyl alcohol 9 which was easily converted to L-deoxyaltronojirimycin by regioselective ring opening.

• Proceedings of the PSK Conference
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• 2002.10a
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• pp.233.1-233.1
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• 2002

Azasugars, which have been called the "sugar-shaped" alkaloids from plants. are reversible. competitive inhibitors of glycosidases. The purpose of these natural products is possibly to inhibit the carbohydrate metabolism and consequently the growth of plant consuming pests. Since selective glycosidase inhibitors have a large number of interesting potential applications including treatment of AIDS, diabetes. and tumor metastasis. they have received a considerable attentions. (omitted)