Synthesis of Biologically Active Nitrogen Containing Aliphatic Compounds Using Nitroethanol as a Synthon.

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A novel types of biologically active nitrogen containing compounds have been synthesized via the nitroaldol reaction using nitroethanol by our recently developed method as shown below.1. Synthesis of Cerebroside B1a, 1aSynthesis of four diastereoisomeric ceramides including the aglycone cerebroside B1a, 1a, was achieved, one of which was converted to the optically active 1a by glycosylation. Consequently, the absolute configuration of 1a was determined to be (2S,3R,4E,8Z,2'R)-1-0-(beta-D-glucopyranosyl)-N-(2'-hydr-hexadecanoyl)-4, 8-sphingadienine.2. Synthesis of (+)-erythro-N-lauroyldocosasphinga-4, 8-dienine, 2.The racemic 2 was synthesized by the simple method developed by the total synthesis of 1a. Optical resolution gave (+) and (-)-2. We also synthesized the optically active 2 by two different chiral synthesis.3. Synthetic approaches to the pseudodistomins A (3a) and B (3b) novel antineoplastic piperidine alkaloids with calmodulin antagonistic activity from the Okinawan Tunicate Pseudodistoma KanokoWe have established the synthesis of the piperidine ring which has the requisite three substitutents at the proper position by three different approaches.4. Sialidase inhibitor, 5-acetamido-4-hydroxypipecolinic acid 4The compound 4 was synthesized by analogous method used for the synthesis of 3.