Tetrahedron

Combining the [2, 3] sigmatropic rearrangement and ring-closing metathesis strategies for the synthesis of spirocyclic alkaloids. A short and efficient route to (±)- …

D Tanner, L Hagberg, A Poulsen

Index: Tanner, David; Hagberg, Lars; Poulsen, Anders Tetrahedron, 1999 , vol. 55, # 5 p. 1427 - 1440

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Citation Number: 33

Abstract

This paper describes the use of selenium-based [2, 3] sigmatropic rearrangement in combination with ruthenium-catalyzed ring-closing metathesis (RCM) for the synthesis of azaspiro ring systems, as exemplified by the reactions of model substrates 5 and 6. The methodology has been applied to a short and efficient formal total synthesis of the alkaloid (±)-perhydrohistrionicotoxin (2). Thus,(±)-depentylperhydrohistrionicotoxin, 1, a known key ...