Synthese des Colchicins

Schreiber, J.; Leimgruber, W.; Pesaro, M.; Schudel, P.; Threlfall, Terry L.; Eschenmoser, Albert

doi:10.1002/hlca.19610440225

Cited by 119 publications

(31 citation statements)

References 58 publications

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“…Deacetamidocolchicine was made by catalytic reduction (Pd/C in ethyl acetate) of deacetamido-5, 6-dehydrocolchicine, prepared according to [8]. Deacetamidocolchicine, thus prepared, showed chemical and physical properties identical with material obtained by total synthesis [9]. All other chemicals were obtained commercially.…”

Section: Methodsmentioning

confidence: 99%

The importance of the phenyl‐tropolone ‘aS’ configuration in colchicine's binding to tubulin

1988

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Measuring ellipticities of (±)‐colchicine and (±)‐deacetamidocolchicine in the presence of tubulin afforded net positive CD bands with maxima at 340 nm resulting from reduction of the negative ellipticities upon binding of (−) enantiomers to the protein. Results of optical studies together with earlier NMR conformational analysis of these molecules substantiate the hypothesis that colchicinoids bind to tubulin with the phenyl‐tropolone moiety in the ‘aS’ configuration. Natural colchicine which binds to tubulin, therefore, should be referred to as (−)‐(aS, 7S)‐colchicine.

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Section: Methodsmentioning

confidence: 99%

The importance of the phenyl‐tropolone ‘aS’ configuration in colchicine's binding to tubulin

1988

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“…The first successful total synthesis of (AE)-colchicine by Eschenmoser [1,2] was reported in 1959 using commercially available purpurogallin as the starting material. The sequence of reactions with fairly detailed experimental conditions is delineated in Fig.…”

Section: The Pioneering Eschenmoser Synthesismentioning

confidence: 99%

Colchicine, A Phenylethylisoquinoline Alkaloid Derived from L-Tyrosine

Talapatra

2014

Chemistry of Plant Natural Products

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“…On the other hand, intramolecular amide-bond formations were successful employing a lasso technique via the depsipeptides 12a and 12b to produce the substituted secocyclosporins 13a and 13b, respectively. Successful intramolecular transformations where corresponding intermolecular reactions had failed, have been described previously in the literature [21]. As an example of the lasso technique thioamides were used in the total synthesis of vitamin B 12 to form enamines with the extrusion of the S-atom [22].…”

Section: Concludingmentioning

confidence: 99%

Stereoselective Synthesis of [5‐[4,4,4,4′,4′,4′‐Hexafluoro‐N‐(2‐hydroxyethoxy)‐D‐valine]]‐ and [5‐[4,4,4,4′,4′,4′‐Hexafluoro‐N‐(2‐hydroxyethoxy)‐L‐valine]cyclosporin A

Eberle

Keese

2010

Helvetica Chimica Acta

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Addition of various amines to the 3,3‐bis(trifluoromethyl)acrylamides 10a and 10b gave the tripeptides 11a–11f, mostly as mixtures of epimers (Scheme 3). The crystalline tripeptide 11f2 was found to be the N‐terminal (2‐hydroxyethoxy)‐substituted (R,S,S)‐ester HOCH2CH2O‐D‐Val(F6)‐MeLeu‐Ala‐OtBu by X‐ray crystallography. The C‐terminal‐protected tripeptide 11f2 was condensed with the N‐terminus octapeptide 2b to the depsipeptide 12a which was thermally rearranged to the undecapeptide 13a (Scheme 4). The condensation of the epimeric tripeptide 11f1 with the octapeptide 2b gave the undecapeptide 13b directly. The undecapeptides 13a and 13b were fully deprotected and cyclized to the [5‐[4,4,4,4′,4′,4′‐hexafluoro‐N‐(2‐hydroxyethoxy)‐D‐valine]]‐ and [5‐[4,4,4,4′,4′,4′‐hexafluoro‐N‐(2‐hydroxyethoxy)‐L‐valine]]cyclosporins 14a and 14b, respectively (Scheme 5). Rate differences observed for the thermal rearrangements of 12a to 13a and of 12b to 13b are discussed.

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Synthese des Colchicins

Abstract: Es wird eine von Purpurogallin, bzw. Pyrogallol ausgehende Totalsynthese des Colchicins, des Hauptalkaloids der Herbstzeitlose, beschrieben.

Cited by 119 publications

References 58 publications

The importance of the phenyl‐tropolone ‘aS’ configuration in colchicine's binding to tubulin

The importance of the phenyl‐tropolone ‘aS’ configuration in colchicine's binding to tubulin

Colchicine, A Phenylethylisoquinoline Alkaloid Derived from L-Tyrosine

Stereoselective Synthesis of [5‐[4,4,4,4′,4′,4′‐Hexafluoro‐N‐(2‐hydroxyethoxy)‐D‐valine]]‐ and [5‐[4,4,4,4′,4′,4′‐Hexafluoro‐N‐(2‐hydroxyethoxy)‐L‐valine]cyclosporin A

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