Tetrahedron p. 3195 - 3202 (1988)
Update date:2022-08-03
Topics:
Gribble, Gordon W.
Barden, Timothy C.
Johnson, David A.
A synthesis protocol involving beta-lithiation of 2-(2-pyridinyl)indoles(4<*>5) and subsequent reaction with bromoacetaldehyde leads to the indolo<2,3-a>quinolizine (1) ring system.Application of this methodology to 2-(2-pyridinyl)indole 17, which is prepared via Taylor-Boger triazine Diels-Alder annulation chemistry, affords the zwitterionic indole alkaloid sempervirine (3).
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Doi:10.1248/cpb.36.1139
(1988)Doi:10.1021/jo901350j
(2009)Doi:10.1055/s-0029-1217329
(2009)Doi:10.1002/ejic.200800524
(2008)Doi:10.1248/cpb.39.1736
(1991)Doi:10.1016/S0040-4039(00)87824-7
(1988)
