Practical synthesis of Boc and Fmoc protected 4-fluoro and 4-difluoroprolines from trans-4-hydroxyproline
1998; Elsevier BV; Volume: 39; Issue: 10 Linguagem: Inglês
10.1016/s0040-4039(97)10793-6
ISSN1873-3581
AutoresLuc Demange, Andre Ménèz, Christophe Dugave,
Tópico(s)Chemical Synthesis and Analysis
ResumoBoc-cis-4-fluoro-L-proline and 4-difluoro-L-proline, usable in classical peptide synthesis, were obtained in respectively 71% (3 steps) and 65% (4 steps) overall yields from the readily available trans-4-hydroxy-L-proline methyl ester. The corresponding fluorinated trans-isomer was isolated in 24% yield (5 steps). Transformation of Boc-protected compounds to their Fmoc-equivalents was performed in high yields.
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