Cycloaddition Protocol for the Assembly of the Hexacyclic Framework Associated with the Kopsifoline Alkaloids

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2006 Oct 20

PMID 17048863

Citations 3

Authors

Xuechuan Hong

Stefan France

Jose M Mejia-Oneto

Albert Padwa

Affiliations

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Abstract

An approach to the hexacyclic framework of the kopsifoline alkaloids has been developed and is based on a Rh(II)-catalyzed cyclization-cycloaddition cascade. The resulting [3+2]-cycloadduct was readily converted into the TBS enol ether 23. Oxidation of the primary alcohol present in 23 followed by reaction with CsF afforded compound 24 that contains the complete hexacyclic skeleton of the kopsifolines. [reaction: see text]

Citing Articles

The Latest Progress in the Chemistry of Alkaloids.

Chen L, Lv C, Meng Y, Yang Z, Xin W, Zhu Y Molecules. 2024; 29(23).

PMID: 39683658 PMC: 11643463. DOI: 10.3390/molecules29235498.

Total syntheses of (-)-kopsifoline D and (-)-deoxoapodine: divergent total synthesis via late-stage key strategic bond formation.

Lee K, Boger D J Am Chem Soc. 2014; 136(8):3312-7.

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A Dipolar Cycloaddition Approach Toward the Kopsifoline Alkaloid Framework.

Hong X, France S, Padwa A Tetrahedron. 2007; 63(26):5962-5976.

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