188198-67-6Relevant articles and documents
Total synthesis of pinnamine and anatoxin-a via a common intermediate. A caveat on the anatoxin-a endgame
Hjelmgaard, Thomas,Sotofte, Inger,Tanner, David
, p. 5688 - 5697 (2007/10/03)
This paper describes the total synthesis of the naturally occurring alkaloids pinnamine (1) and anatoxin-a (2) from a common enantiomerically pure intermediate (7) easily available from pyroglutamic acid. The synthesis of enantiopure pinnamine proceeded in 10 steps and 4.8% overall yield, and the route was flexible enough to allow stereocontrolled access to a non-natural congener (5-epi-pinnamine) of the natural product. Intramolecular reaction of an N-acyl iminium ion was a key step in the synthesis of both pinnamine and anatoxin-a. However, in stark contrast to literature precedent, complete racemization was observed during the reaction of the N-acyliminium ion leading to the latter alkaloid.
Enantioselective construction of highly functionalized indoloquinolizines-congeners to polycyclic indole alkaloids
Lock, Ralf,Waldmann, Herbert
, p. 143 - 151 (2007/10/03)
Indolo[2,3-α]quinolizines have been prepared in enantiomerically pure form by a very short and efficient synthetic sequence consisting of a) formation of imines of tryptophan esters, b) their enantioselective reaction with substituted silyloxydienes media
