Tetrahedron

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

GW Gribble, TC Barden, DA Johnson

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

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被引用次数: 37

摘要

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).