Synthesis of the tetracyclic skeleton of the galanthamine-type Amaryllidaceae alkaloids

Abstract

The hexahydrobenzofurobenzazepine tetracycle characteristic of the principal galanthamine-type Amaryllidaceae alkaloids was synthesized from a methoxy substituted 2-tetralone via simple and convenient reaction steps.

Amaryllidaceae and Sceletium alkaloids

“…92 In addition, various synthetic strategies toward the total synthesis of galanthamine-type alkaloids have been devised. 93,94 2.3.5 Montanine-type alkaloids. Enantiomerically enriched g-nitroketones 142, prepared via an organocatalytic Michael reaction, were versatile building blocks for the synthesis of cisand trans-octahydroindoles 143, which was an advanced precursor in the total synthesis of the alkalolid (À)-pancracine 58.…”