Asymmetric synthesis of proline-based conformationally constrained tryptophan mimetic.
The synthesis of an optically pure proline-based tryptophan mimetic is described. The strategy involves the in situ generation of an unprecedented allylmetal species containing the indole moiety, and its coupling with a chiral imine. The construction of the 3-substituted proline skeleton is then achieved through a hydrozirconation/iodination sequence applied to the resulting homoallylic amine.
Delaye
Pierre-Olivier
PO
ICMR, CNRS-UMR 6229, Université de Reims Champagne-Ardenne, BP 1039, 51687, Reims Cedex 2, France.
Vasse
Jean-Luc
JL
Szymoniak
Jan
J
D040761:Biomimetic Materials / Q000138:chemical synthesis*; D007455:Iodine / Q000737:chemistry; D015394:Molecular Structure; D011392:Proline / Q000737:chemistry*; D013237:Stereoisomerism; D014364:Tryptophan / Q000737:chemistry*
D014364:Tryptophan; D007455:Iodine; D011392:Proline