Communication

A Biomimetic Route to the Peptide Alkaloid Anachelin^†

Karl Gademann Dr.

[email protected]

Laboratorium für Organische Chemie, Eidgenössische Technische Hochschule Zürich, ETH Hönggerberg, 8093 Zürich, Switzerland, Fax: (+41) 1-632-1328

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Yann Bethuel,

Yann Bethuel

Laboratorium für Organische Chemie, Eidgenössische Technische Hochschule Zürich, ETH Hönggerberg, 8093 Zürich, Switzerland, Fax: (+41) 1-632-1328

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Karl Gademann Dr.,

Karl Gademann Dr.

[email protected]

Laboratorium für Organische Chemie, Eidgenössische Technische Hochschule Zürich, ETH Hönggerberg, 8093 Zürich, Switzerland, Fax: (+41) 1-632-1328

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Yann Bethuel,

Yann Bethuel

Laboratorium für Organische Chemie, Eidgenössische Technische Hochschule Zürich, ETH Hönggerberg, 8093 Zürich, Switzerland, Fax: (+41) 1-632-1328

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First published: 16 June 2004

https://doi.org/10.1002/anie.200453909

Citations: 26

^†

K.G. thanks Prof. Dr. E. M. Carreira for generous financial support, as well as the Roche Research Foundation and the Schweizerischer Nationalfonds.

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Graphical Abstract

A postulated biogenesis forms the basis for a synthetic route to the natural product anachelin H (1). Key steps include a tellurium-mediated, oxidative aza annulation and a Claisen condensation under mild conditions. Experiments with a model substrate indicate that it is likely that a catechol oxidase-type enzyme is involved in the biosynthesis of the anachelin chromophore.

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References

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14A reference sample of 23 was prepared by chemical oxidation of 6 using dianisyltellurium oxide and characterized: (UV: λ_max=284 nm, ε=3960 M⁻¹ s⁻¹, shoulder at λ=305 nm, ε=850 M⁻¹ s⁻¹).
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Volume43, Issue25

June 21, 2004

Pages 3327-3329

A Biomimetic Route to the Peptide Alkaloid Anachelin^†

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A Biomimetic Route to the Peptide Alkaloid Anachelin^†