Mass spectrometry in structural and stereochemical problems. Vincadifformine (alcaloïdes des pervenches)

✍ Scribed by Carl Djerassi; H. Budzikiewicz; J.M. Wilson; Janine Gosset; Jean Le Men; Maurice-Marie Janot

• Publisher: Elsevier Science
• Year: 1962
• Tongue: French
• Weight: 227 KB
• Volume: 3
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)70477-1

✦ Synopsis

A RECENT investigation2 of the leaves of Vinca difformis has led to an alkaloid mixture, which could be resolved upon chromatography. One of the new alkaloids, vincadifformine, forms the subject of the present communication since its biogenetically very interesting structure (I) was elucidated largely by means of mass spectrometry. The empirical formula C21 26 2 2 H N 0 (338) of vincadifformine (m.p. l24-125'; [a]D 0') was confirmed by the mass spectrometrically determined molecular weight (molecular ion at m/e 338), while its racemic nature was proved by the observation that the alkaloid exhibited zero rotation (c, 0.077 in methanol) in the region 700-370 mP. The ultraviolet (1::: 225, 300 and 328 mP, log s 3.97, 4.03, 4.19) and infrared (AZ'3 6.0 and 6.15~) spectra suggested the presence of the chromophoric system found in akuam-Part VII. For paper VI see L.