Die Konfiguration des Colchicins und verwandter Verbindungen

Corrodi, H.; Hardegger, E.

doi:10.1002/hlca.19550380743

Cited by 71 publications

(27 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Miravitlles, Solans, Blade-Font, Germain & Declercq (1982) show a figure and some torsion angles corresponding to (7S)-colchiceine acetate but their table inverts the values for comparison with the previous literature. Since unnatural colchicine is not readily available, it seems probable that all of the compounds have the 7S configuration which was established for colchicine itself by Corrodi & Hardegger (1955) (Lessinger & Margulis, 1978b); (4) colchiceine (Silverton, 1979); (5)N-acetyldemecolcine (this paper).…”

mentioning

confidence: 81%

Structure of (7S)-N-acetyldemecolcine, C23H27NO6

Silverton¹,

Sharma²,

Brossi³

1985

Acta Crystallogr C

View full text Add to dashboard Cite

mentioning

confidence: 81%

Structure of (7S)-N-acetyldemecolcine, C23H27NO6

Silverton¹,

Sharma²,

Brossi³

1985

Acta Crystallogr C

View full text Add to dashboard Cite

“…In fact, the elucidation of the chemical structure and the biosynthesis of colchicine represent historic achievements in natural product chemistry. [8] The biosynthesis of colchicine was puzzling in the beginning, because the unusual ring system did not show any clear relationship to other types of plant alkaloids. After investigations by Zeisel (1883Zeisel ( -1913, which led to the development of a method for the determination of methoxy groups, [4] Windaus (1910Windaus ( -1924 made some more specific structural proposals, which were erroneously based on a phenanthrene ring system (2).…”

Section: Structure Elucidation and Biosynthesismentioning

confidence: 99%

“…[6b] The correct structure of colchicine was confirmed in 1952 by means of X-ray crystal-structure analysis, [7] and the absolute configuration was proven by chemical degradation. [8] The biosynthesis of colchicine was puzzling in the beginning, because the unusual ring system did not show any clear relationship to other types of plant alkaloids. Many different hypotheses were put forward before the groups of Leete and, in particular, Battersby proposed the currently accepted biosynthetic route based on a large number of labeling and incorporation experiments.…”

Section: Structure Elucidation and Biosynthesismentioning

confidence: 99%

Total Syntheses of Colchicine in Comparison: A Journey through 50 Years of Synthetic Organic Chemistry

2004

View full text Add to dashboard Cite

Colchicine, the major alkaloid of the meadow saffron, is one of the most prominent natural products and, like other tubulin-binding natural products (e.g. taxol and the epothilones), exhibits great pharmaceutical potential. The first syntheses in the late 1950s were milestones in natural product synthesis. But even today this structurally supposedly simple molecule poses a challenge to synthetic chemists. Only in the last years have syntheses been developed that are efficient enough to provide novel structurally modified colchicine analogues. The comparative examination of all known colchicine total syntheses undertaken in this Review not only reveals the tremendous progress in synthetic organic methodology over the past decades, but also shows how the unique synthetic problems posed by this molecule can be solved in an exceptionally creative manner. Only a few target molecules have been synthesized in such multifaceted ways.

show abstract

“…The correct structure with cycloheptatrienolone moiety was confirmed by X-ray analysis of its crystal [16], and the absolute configuration of its only chiral center has been shown to be (S) by chemical correlation [17]: Colchicine is subjected to ozonolysis, followed by permanganate oxidation of the ozonolysis product to yield (-)-N-acetylglutamic acid of known structure and absolute configuration (S) ( Fig. 24.1).…”

mentioning

confidence: 98%