The synthesis of substances allied to cotarnine / by Arthur H. Salway.

  • Salway, Arthur Henry.
Date:
1909
Catalogue details

Licence: Attribution 4.0 International (CC BY 4.0)

Credit: The synthesis of substances allied to cotarnine / by Arthur H. Salway. Source: Wellcome Collection.

Provider: This material has been provided by The Royal College of Surgeons of England. The original may be consulted at The Royal College of Surgeons of England.

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    a convenient starting-point for the synthesis of cotarnine, the constitution of which has been the subject of considerable discussion. Koser {Annalen, 1888, 249, 156), on the one hand, in consideration of the fact that cotarnine behaves both as an aldehyde and a secondary amine, assigns to it the formula (I), whilst its hydrochloride, which is formed with elimination of the elements of water, is given the formula (II). Decker {J. pr. Chem., 1893, [ii], 47, 222), on the other hand, draws attention to the improbability of the co-existence of an aldehydic residue and a secondary amino-group in the same molecule, and points out that Roser’s formula does not explain why cotarnine is precipitated from its hydrochloride in the aldehydic form, or why hydrocotarnine (III) is converted into cotarnine on oxidation. For these reasons, Decker proposes formula (IV). nTT ^Oi^iCHo-CK-NHMe „„ .o/\cH,-CH, Jcho 2 T CH,< OMe (I.) •O/NcHg-CH, ol^^DHg-NMe OMe (III.) 'CH^NMeCl OMe n/Xcn!- ^^Ol^CH(OH)-NMe- ^le (IV.) With the object of effecting the synthesis of cotarnine from, myristicin, the first experiments consisted in preparing methoxy- methylenedioxy-a-hydrindone, which was obtained according to the- following scheme of reactions ; OHO <0 —^ CHICH-COjH OMe Myristicinaldehyde. \/ OMe 3-Methoxy-4: 5-methylenedioxy- cinnamic acid. ch2<oI 4^ OMe Methoxymethylenedioxy-a- hydrindone. * OMe )8-3-Methoxy-4:6-inethylenedioxy- pheaylpropionic acid. * Of the two possible formula; for methoxymethylenedio.\y-a-hydrindone, namely r OMe CH2<g|^^gg^>CH2 and CH2<ol^?5><^Ho, OMe ‘he former has been adopted throughout this communication. The same applies to