Biosynthesis of chimonanthine from [2-3H]tryptophan and [2-3H]tryptamine

Kirby, G. W.; Shah, Sayed Wadal; Herbert, E. J.

doi:10.1039/j39690001916

Cited by 22 publications

(17 citation statements)

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“…In 1969, Kirby et al provided experimental evidence for the incorporation of isotopically labeled precursors into (-)-chimonanthine (-)-2 (Scheme 2). 13 The results of these feeding experiments using doubly labeled tryptamine 14 and racemic tryptophan 15 are consistent with the oxidative dimerization hypothesis outlined in Scheme 1 for the biosynthesis of calycanthaceous alkaloids.…”

Section: A Biosynthetic Hypothesis For Calycanthaceous Alkaloidssupporting

confidence: 78%

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New Strategies for the Synthesis of Hexahydropyrroloindole Alkaloids Inspired by Biosynthetic Hypotheses

Schmidt¹,

Movassaghi²

2008

Synlett

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Section: A Biosynthetic Hypothesis For Calycanthaceous Alkaloidssupporting

confidence: 78%

“…13 The results of these feeding experiments using doubly labeled tryptamine 14 and racemic tryptophan 15 are consistent with the oxidative dimerization hypothesis outlined in Scheme 1 for the biosynthesis of calycanthaceous alkaloids.…”

Section: A Biosynthetic Hypothesis For Calycanthaceous Alkaloidssupporting

confidence: 78%

New Strategies for the Synthesis of Hexahydropyrroloindole Alkaloids Inspired by Biosynthetic Hypotheses

Schmidt¹,

Movassaghi²

2008

Synlett

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“…Radioactive calycanthine and folicanthine are procured from Calycanthus floridus fed with (AE )- [b-14 C]-tryptophan, [47,48] H]-tryptamine are both converted into chimonanthine in leaf-bearing shoots of Chimonanthus fragrans. [49] A oneelectron oxidation of a tryptamine gives rise to a possible mechanism by which linked cyclotryptamine units could arise biosynthetically. [50] For example, radical cation 17 could lose a proton to form radical 18/19 (Scheme 2).…”

Section: Biosynthesis Of Cyclotryptamine Alkaloidsmentioning

confidence: 99%

Total Synthesis of Complex Cyclotryptamine Alkaloids: Stereocontrolled Construction of Quaternary Carbon Stereocenters

2007

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Our ability to access the more complex members of the cyclotryptamine family of alkaloids, and to exploit their disparate biological activities, is limited by the synthetic challenge posed by their oligomeric, polyindoline structures. A recurring structural theme within these molecules is the presence of multiple quaternary stereocenters in close proximity to one another. Over the last decade, we have developed a set of transformations that allow rapid access to polyindolines, a number of which exploit the ability of catalytic levels of palladium to orchestrate carbon-carbon bond formation with impressive levels of regio- and stereocontrol. This review tells the story behind the development of this toolbox of synthetic methods, and their validation through the total synthesis of a number of structurally complex cyclotryptamine alkaloids. It also highlights an aspect of asymmetric catalysis that has received little attention, the ability of catalytic asymmetric reactions to selectively elaborate complex, polyfunctional molecules.

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“…Die Rolle von Tryptophan und Tryptamin als Biosynthesevorstufen wurde durch Markierungsexperimente belegt. Nach Düngen von Calycanthus floridus mit (±)‐[β‐ 14 C]‐Tryptophan wurde 14 C‐markiertes Calycanthin und Folicanthin isoliert,47, 48 und in den laubtragenden Austrieben von Chimonanthus fragrans werden (±)‐[β‐ 14 C,2‐ 3 H]‐Tryptophan und [β‐ 14 C,2‐ 3 H]‐Tryptamin beide in Chimonanthin umgewandelt 49. Ausgangspunkt für einen möglichen Biosynthesemechanismus ist die Einelektronenoxidation von Tryptamin (Schema ) 50.…”

Section: Biosynthese Der Cyclotryptaminalkaloideunclassified

Totalsynthese komplexer Cyclotryptaminalkaloide: stereokontrollierter Aufbau quartärer Kohlenstoffstereozentren

Steven¹,

Overman²

2007

Angewandte Chemie

129

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Die Cyclotryptamine sind eine Familie von Alkaloiden mit sehr unterschiedlichen biologischen Aktivitäten. Die komplexeren Mitglieder dieser Naturstoffklasse sind durch benachbarte quartäre Kohlenstoffzentren charakterisiert und wegen der schwierig aufzubauenden, oligomeren Polyindolinstruktur schwer zugänglich. In den letzten Jahren konnten wir eine Reihe von Methoden entwickeln, die einen einfachen Zugang zu Polyindolinen ermöglichen; einige dieser Methoden nutzen Palladiumkatalysatoren zum Aufbau von Kohlenstoff‐Kohlenstoff‐Bindungen mit beeindruckenden Regio‐ und Stereoselektivitäten. In diesem Aufsatz schildern wir die Entwicklung eines Repertoires an Synthesemethoden und deren Anwendung in den Totalsynthesen einiger strukturell komplexer Cyclotryptamine. Insbesondere zeigen wir auf, wie es gelingen kann, mithilfe asymmetrischer Katalysen komplexe, hochfunktionalisierte Moleküle aufzubauen.

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Biosynthesis of chimonanthine from [2-3H]tryptophan and [2-3H]tryptamine

Abstract: Jtoridzts from [c~-~~C]tryptophan without ' scrambling ' of the radio-label. Sy utthesis of Preczcrsors .-[2-2H]and [e3H] -I ndole

Cited by 22 publications

References 0 publications

New Strategies for the Synthesis of Hexahydropyrroloindole Alkaloids Inspired by Biosynthetic Hypotheses

New Strategies for the Synthesis of Hexahydropyrroloindole Alkaloids Inspired by Biosynthetic Hypotheses

Total Synthesis of Complex Cyclotryptamine Alkaloids: Stereocontrolled Construction of Quaternary Carbon Stereocenters

Totalsynthese komplexer Cyclotryptaminalkaloide: stereokontrollierter Aufbau quartärer Kohlenstoffstereozentren

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