Total Synthesis of Dimeric Alkaloids (-)-flueggenines D and I

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2021 Jun 14

PMID 34123190

Citations 3

Authors

Sangbin Jeon

Jinwoo Lee

Sangbin Park

Sunkyu Han

Affiliations

Soon will be listed here.

Abstract

We describe the total synthesis of (-)-flueggenines D and I. This features the first total synthesis of dimeric alkaloids with a C(α)-C(δ') connectivity between two monomeric units. The key dimerization was enabled by a sequence that involves Stille reaction and conjugate reduction. The high chemofidelity of the Stille reaction enabled us to assemble two structurally complex fragments that could not be connected by other methods. Stereochemical flexibility and controllability at the δ'-junction of the dimeric intermediate render our synthetic strategy broadly applicable to the synthesis of other high-order alkaloids.

Citing Articles

Total synthesis of (-)-flueggenine A and (-)-15'--flueggenine D.

Seo S, Kim D, Kim T, Han S Chem Sci. 2024; 16(3):1216-1221.

PMID: 39677935 PMC: 11635435. DOI: 10.1039/d4sc07525k.

Interaction of Norsecurinine-Type Oligomeric Alkaloids with α-Tubulin: A Molecular Docking Study.

Vergoten G, Bailly C Plants (Basel). 2024; 13(9).

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Transformation of (allo)securinine to (allo)norsecurinine via a molecular editing strategy.

Kim S, Lee H, Han S Front Chem. 2024; 12:1355636.

PMID: 38318111 PMC: 10839145. DOI: 10.3389/fchem.2024.1355636.

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