Tetrahedron

Indole alkaloids. A combined chemical and enzymatic route for eburnane ring construction: Formal synthesis of (−)-Eburnamonine

G Palmisano, P D'Anniballe, M Santagostino

Index: Palmisano, Giovanni; D'Anniballe, Paolo; Santagostino, Marco Tetrahedron, 1994 ,  vol. 50,  # 31  p. 9487 - 9494

Full Text: HTML

Citation Number: 15

Abstract

A stereocontrolled formal synthesis of (−)-eburnamonine 1, a tetracyclic indole alkaloid used as antihypertensive drug, has been achieve through the use of [3, 3]-sigmatropic rearrangement (Claisen rearrangement) of the enantiopure β-alkoxy acrylate 4, available from rac-3-ethly-cyclohexenol 3via lipase-catalyzed transesterification