55803-41-3Relevant articles and documents
A Modular Access to (±)-Tubocurine and (±)-Curine - Formal Total Synthesis of Tubocurarine
Otto, Nicola,Ferenc, Dorota,Opatz, Till
, p. 1205 - 1217 (2018/06/18)
Two consecutive Cu-catalyzed Ullmann-type C-O couplings permitted the first successful entry toward the curare alkaloids (±)-tubocurine and (±)-curine. Starting from vanillin, the synthetic sequence comprises 15 linear steps and includes a total of 24 transformations. In addition, the total synthesis of tubocurine represents a formal total synthesis of the famous arrow poison alkaloid tubocurarine.
Formal synthesis of the bisbenzylisoquinoline alkaloid berbamunine by asymmetric substitution of chiral organolithium compounds
Gawley, Robert E.,Smith, Gregory A.
experimental part, p. 167 - 179 (2011/07/07)
Asymmetric alkylation of enantiomeric tetrahydroisoquinolyl oxazolines was achieved with 96-97% diastereoselectivity. Removal of the oxazoline chiral auxiliary and further transformations provide a straightforward synthesis of the two synthetic intermediates that were previously synthesized by resolution, and which comprise a formal synthesis of berbamunine by Ullman coupling. ARKAT-USA, Inc.
An efficient synthesis of thalifoline
Wang, You-Chu,Georghiou, Paris E.
, p. 2187 - 2190 (2007/10/03)
An efficient multi-step approach for the synthesis of the isoquinolin-1-one alkaloid thalifoline (1) is described. The key intermediate carbamate 8a underwent a modified Bischler-Napieralski-type cyclization using Banwell's Tf2O/DMAP conditions to form the lactam 9a under mild conditions and in excellent yield.