Premium
Synthesis of (±)‐Strychnofoline via a Highly Convergent Selective Annulation Reaction
Author(s) -
Lerchner Andreas,
Carreira Erick M.
Publication year - 2006
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200600957
Subject(s) - aldimine , annulation , diastereomer , yield (engineering) , ring (chemistry) , chemistry , mathematics , mannich reaction , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , materials science , metallurgy
Studies aimed at preparing (±)‐strychnofoline by total synthesis are detailed. The route described makes use of a recently developed MgI 2 ‐mediated ring‐expansion reaction of spiro[cyclopropan‐1,3′‐oxindole] with a cyclic disubstituted aldimine. The ring‐expansion product was formed as a single diastereoisomer in 55 % yield, possessing the same stereochemical pattern found in strychnofoline. In addition, our synthetic effort has led to the development of new reaction methodology to access 3,4‐disubstituted cyclic aldimines.