St(+)-Ipalbidine. [a]~+-.54.1° (c= 1, ethanol) as hydrobromide, was synthesized from natural (Stproline with retention of configuration. The hldrobromide of the synthetic product was identical in all respects with that of the OptiC3lly active natural ipalbidine isolated from the Chinese species Tpomoea fiordwickii Hemsl.Hua Tuo Dou (follow the name of an ancient famous Chinese surg-.on Hua Tuo) are the seeds of Ipomoea hardwickii Hemsl, and have been used in the folk medicine of South China as an analgesic for years, It was interesting that the ipalbidine(1)' isolated therefrom appeared optically active, in contrast to the racemic form from ljmmmz species indigenous to other parts of the world.2h So far, (itipalbidine has been synthesized -by six groups' and resolved to (ftipalbidine, which was used furthsr for the synthesis of naturally occurring (+)-ipalbine (21.93We haw synthesized (Sj(+)-ipaltidine from the optically active natural (S)-proline 3 by reaction illustrated in Scheme 1 with retention of configuration.
Scheme 1H 3
This paper reports two novel facile approaches to the total synthesis of (±)‐linalool. One of them consisted of a three‐step sequence starting from 3‐acetyl‐propanol and gave an over‐all yield of 59%, and the other started from 1,3‐propanediol and (±)‐linalool was obtained in 12% over‐all yield through six steps.
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