Tetrahedron

Application of a catalytic palladium biaryl synthesis reaction, via C–H functionalization, to the total synthesis of Amaryllidaceae alkaloids

JC Torres, AC Pinto, SJ Garden

Index: Torres, Jose C.; Pinto, Angelo C.; Garden, Simon J. Tetrahedron, 2004 , vol. 60, # 44 p. 9889 - 9900

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Citation Number: 73

Abstract

The total synthesis of the Amaryllidaceae alkaloids dehydroanhydrolycorine, hippadine, pratosine, anhydrolycorine, assoanine, anhydrolycorin-7-one and oxoassoanine was achieved from the appropriate N-benzylisatin precursors using an intramolecular, palladium catalyzed, dehydrohalogenation, biaryl synthesis reaction to establish the carbon skeleton of the natural products. In order to avoid the formation of regioisomers in the cyclization ...