By R.H.F Manske, H.L. Holmes
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Additional resources for Alkaloids: Chemistry and Pharmacology, Volume 12
Ethylation of the azomethine (XCIV)was followed 32 S. W. PELLETIER AND L. H. KEITH by epimerization with base to give what was believed t o be 14-dehydro0x0-1-epidelcosine. Sodium borohydride reduction of the latter followed by reduction with lithium aluminum hydride supposedly yielded 1-epidelcosine. Actually, the epimerization reaction gave back the original C- 1 epimer (64) 14-dehydrooxodelcosine (XCVII). Sodium borohydride reduction of the latter surprisingly gave oxoepi-14-delcosine (XCVIII)!
The formation ofa y-lactone in the periodate oxidation of demethyleneoxodeltamine (LII) and the fact that deltamine (XLVIII) is stable t o periodate oxidation unequivocally determines the position of the hydroxyl a t C-10. Since this hydroxyl was eliminated in the conversion of deltaline to delpheline, it seemed possible to represent the structure of deltaline as XLIII with some assurance. However, further experimentation by Carmack (36)cast doubt on the skeletons of deltaline, deltamine, and delpheline.
Table VI lists the recently reported derivatives of delcosine. E. The reactions of delsoline are quite similar to those of delcosine. Thus, the formation of a carbinolamine 36 S. W. PELLETIER AND L. H. KEITH ether showed the presence of a secondary hydroxyl in ring A which was assumed to be a t C-1. Oxidation with mercuric acetate produced anhydrohydroxy-N-desethyldelsolinewhich could be realkylated with ethyl iodide, showing the presence of an N-ethyl group. And O-acetyloxodelsoline is cleaved by lead tetraacetate to a secodiketone that loses methanol on recrystallization, demonstrating the presence of two vicinal tertiary hydroxyls, one of which is CL to a methoxyl group.
Alkaloids: Chemistry and Pharmacology, Volume 12 by R.H.F Manske, H.L. Holmes