Fluoroolefin dipeptide isosteres synthesis

T. Allmendinger, E. Felder, E. Hungerbuehler, Fluoroolefin dipeptide isosteres. II. Enantioselective synthesis of both antipodes of the Phe-Gly dipeptide mimic. Tetrahedron Lett. 31 (1990) 7301-7304. 

Watanabe, D., Koura, M., Saito, A., et al. (2005). A highly stereoselective synthesis of fluoroolefin dipeptide isostere. 125th Annual Meeting of the Pharmaceutical Society of Japan, Tokyo, Japan. Pharmaceutical Society of Japan, Abstract 31-0205. 

Synthesis of funtionalized (Z)-fluoroalkene-type dipeptide isosteres (36) via Sml2-mediated reduction of y,y-difluoro-ot, -enoates 2.3.19. Reductive formation of fluoroolefins and subsequent conversion to diketopiperazine mimics (71). Nonpeptidic amide bond replacement... 

The synthesis and utility of fluoroolefin peptide isosteres has previously been reviewed [45], The fluoroolefin isostere preparations summarized below are organized by the synthetic method employed to introduce the fluoroolefin rather than by the dipeptide isostere formed. 

The E-selective Horner-Wittig reactions of ethyl 2-fluoro-2-diethyl-phosphonoacetate (441) with 2-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-l-yl)cyclopentanone (442) furnished the corresponding tetra-substituted fluoroolefin (443), the key substrate in synthesis of / flC-Ar-Cbz-Gly- P[(E)-CF=C]-Pro-OH dipeptide isostere (444) (Scheme 134). ... 

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