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Rhodium-Catalyzed Crossed [2+2+2] Cycloaddition with Ynamides: Key-Strategy for the Concise Total Synthesis of 3-Oxygenated Carbazole Alkaloids

Abstract : Total syntheses of a set of naturally occurring 3-oxygenated carbazole alkaloids - 6-chlorohyellazole, carazostatin, carbazomycins A and B - are described. The key-strategy underlines a highly chemo- and regioselective rhodium-catalyzed [2+2+2] cyclotrimerization between appropriately tailored yne-ynamides and 1-methoxypropyne that is stirred by the interplay of stereoelectronic and steric effects allowing the introduction of four ring substituents of the natural carbazoles within a single step and making the overall syntheses short and efficient.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02995341
Contributor : Carole Witulski-Alayrac <>
Submitted on : Monday, November 9, 2020 - 10:11:38 AM
Last modification on : Tuesday, November 10, 2020 - 3:31:07 AM

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Carole Alayrac, Bernhard Witulski. Rhodium-Catalyzed Crossed [2+2+2] Cycloaddition with Ynamides: Key-Strategy for the Concise Total Synthesis of 3-Oxygenated Carbazole Alkaloids. Heterocycles, The Japan Institute of Heterocyclic Chemistry, In press, ⟨10.3987/COM-20-S(K)24⟩. ⟨hal-02995341⟩

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