By R.H.F Manske, H.L. Holmes
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Extra resources for Alkaloids: Chemistry and Pharmacology, Volume 12
Deltaline is the acetyl ester of the amino alcohol deltamine (XLVIII, eldelidine) and treatment of the latter with acid produced demethylenedeltamine (XLIX) (19, 36). It was first believed that in the periodate oxidation of XLIII, 3 moles of NaI03 was consumed and this led to the conclusion that XLIII contains four adjacent hydroxyls (19),an assumption later shown to be incorrect by the same authors (37). Apparently, ~ ~ 22 S. W. PELLETIER AND L. H. KEITH due to the high alkalinity of solutions of XLIII, other groups in addition to the glycol were oxidized.
Occidentale S. Wats (32)and later from D . An alkaloid named eldeline was isolated 20 S. W. PELLETIER AND L. H. KEITH from D . elatum (33),a plant native to the Altai Mountains in the USSR, in 1952. It was then found that delphelatine was identical with eldeline (35),the latter name being retained by the Soviet workers. elatum, retaining the name eldeline. However, since the compound first named deltaline was isolated many years before the same alkaloid called eldeline, it seems proper that the former name be retained and the latter be deleted from the literature.
I n addition, it was learned that ring A of delcosine exists in the boat conformation, in contrast to lycoctonine, which exists in the chair conformation. The difference is accounted for by the fact that intramolecular hydrogen bonding exists between the C-1 hydroxyl and the nitrogen. I n a recent paper Amiya and Shima (64b) have further described the pinacol rearrangement of delcosine and also a novel hydrogenation reaction with its product. Treatment of delcosine (LXXII) with acetyl chloride effected the rearrangement giving anhydrodiacetyldelcosine (CII).
Alkaloids: Chemistry and Pharmacology, Volume 12 by R.H.F Manske, H.L. Holmes