1042908-46-2Relevant academic research and scientific papers
Sterically biased 3,3-sigmatropic rearrangement of chiral allylic azides: Application to the total syntheses of alkaloids
Lauzon, Sophie,Tremblay, Francois,Gagnon, David,Godbout, Cedrickx,Chabot, Christine,Mercier-Shanks, Catherine,Perreault, Stephane,DeSeve, Helene,Spino, Claude
, p. 6239 - 6250 (2008/12/22)
(Chemical Equation Presented) We describe a tandem Mitsunobu/3,3- sigmatropic rearrangement of allylic azides on a chiral auxiliary system that favors one regioisomer thanks to its exceptional steric bias. The sequence may be completed by the oxidative cleavage of the auxiliary or by a ring-closing metathesis reaction that produces a carbo-or heterocycle directly and a recyclable form of the chiral auxiliary. Applications of the methodology to the total synthesis of (+)-coniine, (+)-lentiginosin, and (+)-pumiliotoxin C are reported.
