Premium
Total Synthesis of (−)‐Allosecurinine
Author(s) -
Leduc Andrew B.,
Kerr Michael A.
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200803257
Subject(s) - trifluoromethanesulfonate , yield (engineering) , scheme (mathematics) , enantiomer , computer science , chemistry , combinatorial chemistry , stereochemistry , organic chemistry , mathematics , physics , catalysis , mathematical analysis , thermodynamics
Safe and secure : An efficient methodology which provides access to homochiral 2,5‐ cis pyrrolidines in excellent yields starting from chiral alkoxyamine cyclopropanes was used in the total synthesis of (−)‐allosecurinine (see scheme). The synthesis proceeds with enantiomeric purity in 15 steps with an overall yield of 5 %. OTf: trifluoromethanesulfonate, Boc: tert ‐butoxycarbonyl, PG: protecting group.