Rhodium-Catalyzed Crossed [2+2+2] Cycloaddition with Ynamides: Key-Strategy for the Concise Total Synthesis of 3-Oxygenated Carbazole Alkaloids - Archive ouverte HAL Access content directly
Journal Articles Heterocycles Year : 2021

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.
Fichier principal
Vignette du fichier
carbazole 2020.pdf (748.32 Ko) Télécharger le fichier
Origin : Files produced by the author(s)

Dates and versions

hal-02995341 , version 1 (08-12-2020)

Identifiers

Cite

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, 2021, 103 (1, Spec. Iss.), pp.205-217. ⟨10.3987/COM-20-S(K)24⟩. ⟨hal-02995341⟩
162 View
146 Download

Altmetric

Share

Gmail Facebook X LinkedIn More