title: Synthesis of L-2,3-trans-3,4-cis-Dihydroxyproline Building Blocks for Peptide Synthesis.
abstract: L-2,3-trans-3,4-cis-N-Fluorenylmethoxycarbonyl-3,4-dihydroxy-3,4-O-isopropylidineproline (9) has been prepared from D-gulonolactone in nine steps and an overall yield of 22%. Compound 9 has been converted to its allyl ester 13. Compounds 9 and 13 were investigated as building blocks for the incorporation of dihydroxyproline into peptides, with compound 9 serving as a carboxyl component and compound 13 as a precursor to an amino component for peptide coupling reactions. Their utility was demonstrated by the synthesis of dipeptides 11 and 15.
authors.affiliation: Department of Chemistry, University of Auckland, Private Bag 92019, Auckland, New Zealand.
authors.forename: Claudette A.
authors.initials: CA
authors.lastname: Weir
authors.forename: Carol M.
authors.initials: CM
authors.lastname: Taylor