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The Structure Elucidation of Pseudothiocolchicine

✍ Scribed by Bruno Danieli; Giordano Lesma; Giovanni Palmisano; Renata Riva

Publisher: John Wiley and Sons
Year: 1985
Tongue: German
Weight: 297 KB
Volume: 68
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19850680812

No coin nor oath required. For personal study only.

✦ Synopsis

A colchicine derivative, previously isolated from the reaction of isocolchicine with sodium thiomethoxide in aqueous MeOH, was now identified as I I-(methy1thio)isocolchicine on the basis of 'H-, "C-NMR spectra and chemical correlation. This reaction represents the first example of abnormal nucleophilic displacement (telesubstitution) in the colchicine chemistry.

Colchicine (1) may be regarded as a prototype alkaloid occurring in members of the Liliaceae, especially in meadow saffron (Colchicum autumnale) and in the African climbing lily (Gloriosa superba). Compound 1 has powerful mitotic spindle inhibitory effect that cannot be utilized in the treatment of cancer because of high toxicity, however, is still being widely used for treatment of gout [l].

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