Total synthesis of colchicine modelled on a biogenetic theory

Scott, A. I.; McCapra, Frank; Buchanan, R. L.; Day, A. C.; Young, Douglas W.

doi:10.1016/s0040-4020(01)96977-7

Cited by 38 publications

(12 citation statements)

References 36 publications

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“…By today's standards of synthetic chemistry-highly complex natural products containing novel and often sensitive structural elements are synthesized in the laboratory only a few years after their discovery-the small molecule colchicine (1) appears to be a rather simple target at first glance. [28][29][30][31][32][33][34][35][36][37] However, only in recent years have syntheses been developed that show a satisfying overall efficiency. Since the early syntheses of Eschenmoser and co-workers and van Tamelen and co-workers, new approaches towards colchicine have been brought forward continuously, in most cases following fundamentally different strategies.…”

Section: Target Structure and Classification Of The Total Synthesesmentioning

confidence: 99%

“…[30,32,33,41] Thus, specific methodology for the construction of annulated tropolones is a precondition for any efficient total synthesis. Therefore, its generation forms an integral part of any synthetic strategy.…”

Section: Target Structure and Classification Of The Total Synthesesmentioning

confidence: 99%

“…[30] This synthesis is based on an earlier biosynthetic hypothesis postulating the formation of ring B by oxidative phenol-tropolone coupling. [30] This synthesis is based on an earlier biosynthetic hypothesis postulating the formation of ring B by oxidative phenol-tropolone coupling.…”

Section: The Scott Synthesis Of Desacetamidocolchiceine Through Oxidamentioning

confidence: 99%

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

2004

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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.

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Section: Target Structure and Classification Of The Total Synthesesmentioning

confidence: 99%

Section: Target Structure and Classification Of The Total Synthesesmentioning

confidence: 99%

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

2004

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“…Androcymbine (240) was obtained by photolytic dehydrobromination [247] and the photoPschorr reaction [248]. Colchicine (242) has been synthesized by a number of methods [249][250][251][252][253]. Preparation.…”

Section: Phenethylisoquinoline Alkaloidsmentioning

confidence: 99%

“…Since pretazettine (253) also has a trans B -D ring juncture, it was classified in this group. Pretazettine (253) is converted to tazettine on heating in water at 70 • C. Pharmacological Properties. The alkaloids in this group are relatively nontoxic to mammals.…”

Section: −→ 248 249mentioning

confidence: 99%

Alkaloids

Hoshino¹,

Murakata²,

Ishizaki³

et al. 2000

Ullmann's Encyclopedia of Industrial Chemistry

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Der Stand der Totalsynthese zu Beginn des 21. Jahrhunderts

Nicolaou¹,

et al. 2000

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Ein neues Jahrtausend hat begonnen – Grund genug, sich die Frage zu stellen, welchen Stand die Totalsynthese von Naturstoffen erreicht hat. Dieser Aufsatz möchte eine Antwort geben, indem er die Entwicklung dieser chemischen Disziplin, die Aspekte von exakter Wissenschaft und schöner Kunst in sich vereint, von Anbeginn bis in die heutige Zeit beschreibt; es wird geschildert, wie viel wir in der Wissenschaft der Totalsynthese schon erreicht haben, aber auch, dass dieses Forschungsgebiet den Kinderschuhen gerade erst entschlüpft.

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Total synthesis of colchicine modelled on a biogenetic theory

Cited by 38 publications

References 36 publications

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

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

Alkaloids

Der Stand der Totalsynthese zu Beginn des 21. Jahrhunderts

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