Streamlined Strategy for Scalable and Enantioselective Total Syntheses of the Eburnane Alkaloids

Ramakrishna, Gujjula V.; Pop, Larisa P.; Latif, Zurwa; Suryadevara, Harish K. V.; Santo, Luca; Romiti, Filippo

doi:10.1021/jacs.3c07019

J. Am. Chem. Soc.

2023

DOI: 10.1021/jacs.3c07019

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Streamlined Strategy for Scalable and Enantioselective Total Syntheses of the Eburnane Alkaloids

Gujjula V. Ramakrishna,

Larisa P. Pop,

Zurwa Latif

et al.

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Cited by 8 publications

References 83 publications

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Iridium‐Catalyzed Reductive (3+2) Annulation of Lactams Enabling the Rapid Total Synthesis of (±)‐Eburnamonine

Sugiyama,

Yamada,

Kaneko

et al. 2023

Angewandte Chemie

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A reductive (3+2) annulation of lactams through iridium‐catalyzed hydrosilylation and photoredox coupling with α‐bromoacetic acid was developed. The iridium‐catalyzed hydrosilylation of the lactam carbonyl group and subsequent elimination provide a transient cyclic enamine, which undergoes iridium‐catalyzed photoredox coupling with α‐bromoacetic acid in a one‐pot process. The developed conditions show high functional‐group tolerance and provide cyclic N,O‐acetals containing a quaternary carbon center. The resulting N,O‐acetals undergo a variety of acid‐mediated nucleophilic addition reactions via iminium ions to give substituted cyclic amines. The developed sequence including reductive (3+2) annulation and acid‐mediated nucleophilic addition was successfully applied to the four‐step total synthesis of (±)‐eburnamonine.

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Iridium‐Catalyzed Reductive (3+2) Annulation of Lactams Enabling the Rapid Total Synthesis of (±)‐Eburnamonine

Sugiyama,

Yamada,

Kaneko

et al. 2023

Angewandte Chemie

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Stereodivergent Total Synthesis of Tacaman Alkaloids

Chen,

Wang,

Zeng

et al. 2024

Angewandte Chemie

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This paper describes a concise, asymmetric and stereodivergent total synthesis of tacaman alkaloids. A key step in this synthesis is the biocatalytic Baeyer‐Villiger oxidation of cyclohexanone, which was developed to produce seven‐membered lactones and establish the required stereochemistry at the C14 position (92% yield, 99% ee, 500 mg scale). Cis‐ and trans‐tetracyclic indoloquinolizidine scaffolds were rapidly synthesized through an acid‐triggered, tunable acyl‐Pictet‐Spengler type cyclization cascade, serving as the pivotal reaction for building the alkaloid skeleton. Computational results revealed that hydrogen bonding was crucial in stabilizing intermediates and inducing different addition reactions during the acyl‐Pictet‐Spengler cyclization cascade. By strategically using these two reactions and the late‐stage diversification of the functionalized indoloquinolizidine core, the asymmetric total syntheses of eight tacaman alkaloids were achieved. This study may potentially advance research related to the medicinal chemistry of tacaman alkaloids.

show abstract

Iridium‐Catalyzed Reductive (3+2) Annulation of Lactams Enabling the Rapid Total Synthesis of (±)‐Eburnamonine

Sugiyama,

Yamada,

Kaneko

et al. 2023

Angew Chem Int Ed

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Streamlined Strategy for Scalable and Enantioselective Total Syntheses of the Eburnane Alkaloids

Cited by 8 publications

References 83 publications

Iridium‐Catalyzed Reductive (3+2) Annulation of Lactams Enabling the Rapid Total Synthesis of (±)‐Eburnamonine

Iridium‐Catalyzed Reductive (3+2) Annulation of Lactams Enabling the Rapid Total Synthesis of (±)‐Eburnamonine

Stereodivergent Total Synthesis of Tacaman Alkaloids

Iridium‐Catalyzed Reductive (3+2) Annulation of Lactams Enabling the Rapid Total Synthesis of (±)‐Eburnamonine

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