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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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Extra resources for Alkaloids: Chemistry and Pharmacology, Volume 12

Example text

PELLETIER AND L. H. KEITH which possesses an N-methyl instead of an N-ethyl. Vigorous treatment of aconitine (partial structure CXXIV) with nitrous acid (81a)resulted in the cleavage of the N-ethyl and formation of the nitroso derivative CXXV. Acetylation of cxxv CXXIV * CHaCHz-N 5 OAc 5 OAc H CXXXI CXXXII CXXV with acetyl chloride gave a mixture of CXXVI and its acetolysis product CXXVII in 14% and 57% yields, respectively. Treatment of CXXVI with phosgene produced CXXVIII, which was then converted to the N-formyl derivative CXXIX, a compound identical with an authentic sample of triacetyloxonitine prepared by permanganate oxidation of triacetylaconitine (CXXX).

More recently, aconitine has been isolated from the Chinese drugs Hye-shang-yi-zhi-hao ( A . bullatifolium LBveillB var homotrichum) (72) and Chuan-wu and Fu-tzu (A. carmichaeli Debaux= A . ) (73). The early work done on aconitine is characterized by confusion and, indeed, all but the most recent studies accomplished little more than clarification of the functional groups present in the polycyclic molecule. It was shown that aconitine contains a tertiary nitrogen with an N-ethyl, one acetoxy, one benzoyloxy group, four methoxyls, and three hydroxyls.

Catalytic hydrogenation of CII over platinum yielded dihydroanhydrodiacetyldelcosine (CVb) presumably going through the intermediate CVa. However, CIII was recovered unchanged after being subjected t o the same conditions of hydrogenation. Probably the unavailability of the lactam nitrogen atom’s free electron pair prevented the formation of the intermediate (CVa). Some interesting I R - and UV-spectral features were also observed. 78 p. 93 p. 20). However, amide formation removes the . anomaly and absorption maxima appear near 300 mp and are ascribed t o ketone chrbonyl groups.

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


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