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An asymmetric synthesis of L-pyrrolysine.

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.

SUBMITTER: Wong ML 

PROVIDER: S-EPMC3326344 | biostudies-other | 2012 Mar

REPOSITORIES: biostudies-other

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An asymmetric synthesis of L-pyrrolysine.

Wong Margaret L ML   Guzei Ilia A IA   Kiessling Laura L LL  

Organic letters 20120306 6

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. ...[more]