On the chemical constitution of obacunone

✍ Scribed by T. Kubota; T. Kamikawa; T. Tokoroyama; T. Matsuura

• Publisher: Elsevier Science
• Year: 1960
• Tongue: French
• Weight: 424 KB
• Volume: 1
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)82701-5

✦ Synopsis

SINCE the isolation of obacunone C26H3007(I), a bitter principle of Rutaceae, from Phelledendron amurenae, Rupr. by Murayma and Takata' in 1928, it has been investigated by many workers. l-5 Kaku and Ri2 showed that (I) possessed two lactonea (one, c&-unsaturated) and a keto group. Later Kubota and Tokoroyama4 proved that one of the two remaining oxygens belonged to a furan ring end suggested that the other could be assigned to en ether linkage. In 1958, Dean and Geissmen5 proposed a partial structure (IA) for obacunone based on the results of spectral studies. In continuation of our earlier studies, we should now like to record some observations which lead to the assignment of another partial structure (IB) to this substance. (i) The number of double bonds in abacunone (Scheme 1 and Fig. 1) As a result of ozonization of obacunone hydrochloride (II) three carbons were lost giving ethioobacunoic acid hydrochloride (III) C23H2908C1,