First total synthesis of (−)-dioncophylline A (“Triphyophylline”) and of selected stereoisomers: Complete (revised) stereostructure

doi:10.1016/S0040-4039(00)94589-1

Tetrahedron Letters

Volume 31, Issue 5, 1990, Pages 643-646

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Abstract

The first total synthesis of dioncophylline A (previously “triphyophylline”) and some selected stereoisomers is described, using an intramolecular-type mixed aryl coupling method via ester-type prefixed molecular moieties. Simultaneously, this synthesis establishes the complete (revised) stereostructure of dioncophylline A as 1a, which is thereby the first fully elucidated naphthylisoquinoline alkaloid of Dioncophyllaceae.

The absolute configuration of dioncophylline A (1a, revised structure), is established to be 1R,3R, by its first total synthesis.

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^☆: “Acetogenic Isoquinoline Alkaloids”, part 17; for part 16, see ref. 2.

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Tetrahedron Letters

First total synthesis of (−)-dioncophylline A (“Triphyophylline”) and of selected stereoisomers: Complete (revised) stereostructure☆

Abstract

Phytochem.

Heterocycles

C. R. Acad. Sci. Ser. C

Planta Med. (J. Med. Plant Res.) Suppl.

symposia-in-print of the 6ème Colloque International consacré aux Plantes Médicinales et Substances d'Origine Naturelle, Angers (France)

Accounts Chem. Res.