The structure of digacetigenin : A correction of a recent publication by chandler, coombe, and watson in this journal

✍ Scribed by R. Tschesche; H.G. Berscheid; H.-W. Fehlhaber; G. Snatzke

• Publisher: Elsevier Science
• Year: 1968
• Tongue: French
• Weight: 179 KB
• Volume: 9
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)89535-0

✦ Synopsis

Last year we c21 elucidated the structure of digacetigenin (I) which is in agreement with a proposal made by Shoppee ot al. Csl. Recently Chandler, Coombe, and Watson cl? suggestedmainly on the basis of the mass spectrumthat its structure should be changed to II. This is, however, in dieagreement with most of the chemical and spectroscopical data (27, due to several misinterpretations by these authors cl].

1. From the hi.@! relative intensity of tho peaks M -18 and m/e 43 in the mass spectrum they rll deduced the 17U-II configuration for digacetigenin.

As a reference they used some of our previously published [43 mass spectra (in three cases in*tensities have been cited incorrectly from our plots) of'

compounds which in contrast to digacetigenin do not contain a 15-ketone group.