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

ISBN-10: 0080865364

ISBN-13: 9780080865362

ISBN-10: 0124695124

ISBN-13: 9780124695122

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THE C I S - ALKALOIDS ~ ~ ~ ~ ~ ~21 LIII; R=CHO LIV; R=COOH LII 1 LVI; R 0 LV; R = CHO = CHO, R’ = COOH OAc LVIII line. The unreactivity of this hydroxyl group is demonstrated by the fact that treatment with chromium trioxide in acetic acid for 6 days leads to recovery of part of the alkaloid unchanged, and boiling deltaline with acetyl chloride for 4 hours leaves the bulk of the alkaloid unchanged, indicating that it is a tertiary hydroxyl(19). The stability of deltaline to reduction by lithium aluminum hydride and to catalytic hydrogenation with platinum further showed that the tertiary hydroxyl is not in the same position as in hydroxylycoctonine.

The empirical formula had been establishedasC24H3gNO7 and a lycoctonine-type skeleton was assumed. Of lycoctonine’s seven oxygens, three were known to be present as methoxyl groups and four as hydroxyls. As none of the oxidations produced an acid or aldehyde, it was clear that the analogous C- 18 oxygen functional group of the lycoctonine-type skeleton must be a methoxyl. Carbinolamine ether linkages were rapidly formed with a variety of reagents, leading to the assumption (later shown to be erroneous) (55,60)that C-6 was substituted with a hydroxyl.

PELLETIER AND L. H. KEITH LXIX LXX silver nitrate cannot refute the theory that the halogen is a t the bridgehead (in a lycoctonine-type skeleton) since the cleavage of hydrogen chloride could take place after the rearrangement. 1-bicyclic system in the partial structure LXVIII. It was then concluded that the proposed structures of eldeline and delpheline as LX and L X I (36)were incorrect and that these two alkaloids possessed a lycoctonine-type skeleton after all (38). The unsaturated compound dehydrodesoxydeltaline would then be represented by structure LVIII.

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


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