Tetrahedron

A directed metalation route to the zwitterionic indole alkaloids.: Synthesis of sempervirine

GW Gribble, TC Barden, DA Johnson

Index: Gribble, Gordon W.; Barden, Timothy C.; Johnson, David A. Tetrahedron, 1988 ,  vol. 44,  # 11  p. 3195 - 3202

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Citation Number: 37

Abstract

A synyhesis protocol involving beta-lithiation of 2-(2-pyridinyl) indoles (4→ 5) and subsequent reaction with bromoacetaldehyde leads to the indol [2, 3-a] quinolzine (1) ring system. Application of this methodology to 2-(2-pyridinyl) indole 17, which is prepered via Taylor-Boger triazine Dieis-Alder annulation chemistry, affords the zwitterionic indole alkaloid sempervirine (3).