R.H.F Manske, H.L. Holmes's Alkaloids: Chemistry and Pharmacology, Volume 12 PDF

By R.H.F Manske, H.L. Holmes

ISBN-10: 0080865364

ISBN-13: 9780080865362

ISBN-10: 0124695124

ISBN-13: 9780124695122

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Japwnicum Decne. The alkaloid prcviously reported as Shimoburo base 11,from A . japonicum (56)is identical with 14-dehydro- 1. THE C I S -ALKALOIDS ~ ~ ~ ~ ~ 27~ delcosine (54, 55). The widespread occurrence of delcosine is further attested to by the recent reports of its isolation from Consolida regalis ( 5 7 , l S )and from the seeds of D. orientale (58,59). The first tentative structure put forth for delcosine (46)was LXXI, and it appeared to accommodate the experimental findings a t the time of the previous review ( 2 )in this series.

It was then postulated (36)that a Wagner-Meerwein type of rearrangement had occurred during the acid hydrolysis of XLVI to desoxylycoctonine (XLVII) (31). Due to these discrepancies, the Russians followed up with a more detailed study of the reactions of chlorodeltaline (XLIV) (38). They found that heating XLIV in aqueous alcohol produced the hydrochloride (LXII) of a base isomeric with eldeline (deltaline) and called isoeldeline (isodeltaline). The free base LXIII could be obtained by treatment of 1.

THE C 1 9 - ALKALOIDS ~ ~ ~ ~ ~ ~1 1 ~ structure for lycoctonine (11) followed unambiguously (5). Shortly before publication of the previous review, however, a further study of the X-ray crystallographic data ( 6 ) showed that the absolute configuration of des(oxymethy1ene)lycoctonine hydroiodide monohydrate was the mirror image of I. Thus, the correct representation of lycoctonine is I11 and it should be borne in mind that the structures of all of these compounds mentioned in the previous review are in reality the mirror images of those shown.

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Alkaloids: Chemistry and Pharmacology, Volume 12 by R.H.F Manske, H.L. Holmes


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