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Synthesis 1996; 1996(12): 1463-1467
DOI: 10.1055/s-1996-4425
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Large Scale Syntheses of N-Protected 2,3-Methanomethionine Stereoisomers

Kevin Burgess* , Chun-Yen Ke
  • *Department of Chemistry, Texas A & M University, College Station, TX 77843-3255, USA, Fax +1(409)8454345; E-mail burgess@chemvx.tamu.edu
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Publication History

Publication Date:
31 December 2000 (online)

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Three stereoisomers of N-protected forms of 2,3-methanomethionine (cyclopropyl derivatives of methionine, or ”cyclo-Met”) were prepared. Two of the syntheses developed involved diol (S)-1, which was more easily obtained from L-gulono-1,4-lactone than via juxtaposition of the benzyl protection of (R)-1. The cis-cyclo-Met derivative (cis refers to the orientation of the side chain relative to the amino functionality), FMOC-(2R,3S)-cyclo-Met, was obtained via a route based on a previous synthesis of (2R,3S)-cyclo-Met from the lactone 3, but the protected trans-cyclo-Met, BOC-(2R,3S)-cyclo-Met, was obtained via an improved procedure that does not involve lactone 3.

Gram scale syntheses of the following 2,3-methanomethionine derivatives