Construction of C2-indolyl-quaternary centers by branch-selective allylation: enabling concise total synthesis of the (±)-mersicarpine alkaloid.

Minakshi Ghosh, Samrat Sahu, Shuvendu Saha, Modhu Sudan Maji

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Article in Chemical science, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

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1 citing paper in PubMed.

Stereoselective Copper-Catalyzed Cross-Coupling of α-CFThe Journal of organic chemistry · 2025
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4 authors.

Minakshi GhoshDepartment of Chemistry, Indian Institute of Technology Kharagpur Kharagpur 721302 WB India msm@chem.iitkgp.ac.in.

Samrat SahuDepartment of Chemistry, Indian Institute of Technology Kharagpur Kharagpur 721302 WB India msm@chem.iitkgp.ac.in.ORCID https://orcid.org/0000-0002-9041-472X

Shuvendu SahaDepartment of Chemistry, Indian Institute of Technology Kharagpur Kharagpur 721302 WB India msm@chem.iitkgp.ac.in.ORCID https://orcid.org/0000-0003-2183-9617

Modhu Sudan MajiDepartment of Chemistry, Indian Institute of Technology Kharagpur Kharagpur 721302 WB India msm@chem.iitkgp.ac.in.ORCID https://orcid.org/0000-0001-9647-2683

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Herein we report a branch-selective allylation strategy for accessing C2-indolyl-all-carbon quaternary centers using allylboronic acids. This approach boasts broad functional group tolerance, scalability, and relies on easily accessible allyl alcohol precursors. Importantly, the C3-position of the indole remains free, offering a handle for further synthetic refinement. Mechanistic pathways, corroborated by density functional theory (DFT), suggest the involvement of an indolenine intermediate and a Zimmerman-Traxler-like transition state during allylboration. Demonstrating its efficacy, the method was applied to the total synthesis of the (±)-mersicarpine alkaloid and enabled formal synthesis of additional alkaloids, such as (±)-scholarisine G, (±)-melodinine E, and (±)-leuconoxine.

Identifiers

PMID38303951

DOI10.1039/d3sc04732f

PMCPMC10829033

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