Masateru Miyano

Syntheses and Configurational Analysis of Rotenoids, XIX The Total Synthesis of Natural Rotenone

d,l-Derrisic acid (IIa, R′: H) was synthesized from d,l-hydroxy dihydrotubanol (Ve) by Hoesch condensation with a nitrile (VI). The possible optical resolution of d,l-IIa was demonstrated by a conventional “reversed resolution” method.This communication and previous works constitute the first total synthesis of natural rotenone (Ia).

Studies on Compounds related to Carnitine

Scheme (2)に示した経路でDL-γ-trimethylamino-β-hydroxypropanesulfonic acid (DL-anticarnitineと仮称*)を合成した.

Studies on Chrysanthemic Acid: Part III. Oxidation and Reduction Products of Chrysanthemic Acid

Starting from (±)-cis- and (±)-trans-chrysanthemic acid several oxidation and reduction products were obtained: These are shown in the figure.

Pantothenic Acid and It's Derivatives

A new and improved method is described for synthesis of cystamine hydrochloride. β-Bromoethylamine hydrobromide [II]. was treated with equimolecular amount of thiourea in ethanol to give β-aminoethylisothiouronium bromide [III] quantitatively. The bromide was subjected to alkaline hydrolysis, the reaction mixture was neutralized with sulfuric acid, oxidised with iodine, and the cystamine hydroiodide was converted to hydrochloride thus cystamine hydrochloride was obtained as white crystals. Overall yield was more than 60 per cent from monoethanolamine [I].