Ormosia alkaloids, Part I: structure of ormojanine and ormosanine

✍ Scribed by Z. Valenta; P. Deslongchamps; M.H. Rashid; R.H. Wightman; J.S. Wilson

• Book ID: 104242063
• Publisher: Elsevier Science
• Year: 1963
• Tongue: French
• Weight: 391 KB
• Volume: 4
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)90871-8

✦ Synopsis

Ormosia alkaloids -I No.23 4.55 ]).~a., J 6 ape.). * Controlled hydrogenation of oruojauiue gave dibydro-ormojanine, CseHssI,, r.p. 127.12Q", still containing the double-bond but hating two seoondary nitrogens. Contluued hjdrogenatian esturated the double-bond to give tetr~dre-orusjaulne, CeoHeslVs, n.p. 107~109'. No.23 Omosia alkaloids -' I 1561 and homoqtetrahydro-ormjtine, C,,H,,I,O, m.p. 203-205°, reapeotiw~. !Fheir IR oarbony l baorptlen.(UMO 01" in Ccl,) indioatee that the two 6eoondm-y II'n are separated by at leaat three C at-. The urea grouping was found to be &able to a rigsroer acid and ba8io hydrolyaie, indioating an unatralned,planar arrang8meat. Treatment of dilydro-ormojanine with Pd-ahararal in C,H, at 200' gave a 50s rleld 'of an olu pyridlne, C,,H,,I,. Itr UV apeatrm (infl. 256 mp&_. 262 mp, 0 5,600 and 268 mp, c 5,300, infl. 278 mp) show the prerenoe of two irolated pyridine rinm. The pomitien of these maxima together No.23