2. Academic Validation
  3. An asymmetric synthesis of L-pyrrolysine

An asymmetric synthesis of L-pyrrolysine

  • Org Lett. 2012 Mar 16;14(6):1378-81. doi: 10.1021/ol300045c.
Margaret L Wong 1,  Ilia A Guzei,  Laura L Kiessling
Affiliations

Affiliation

  • 1 Department of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706, United States.
PMID: 22394273 DOI: 10.1021/ol300045c
Abstract

An efficient asymmetric synthesis of the 22nd amino acid L-pyrrolysine has been accomplished. The key stereogenic centers were installed by an asymmetric conjugate addition reaction. A Staudinger/aza-Wittig cyclization was used to form the acid-sensitive pyrroline ring. Pyrrolysine was synthesized in 13 steps in 20% overall yield.

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