High??Yield Synthesis of 20??, 24??, and 28??Membered Macropentolide,??hexolide, and??heptolide, Respectively, from (R)??or (S)??3??hydroxybutanoic acid under …

D Seebach, U Brändli, P Schnurrenberger…

Index: Seebach, Dieter; Braendli, Urs; Schnurrenberger, Peter; Przybylski, Michael Helvetica Chimica Acta, 1988 , vol. 71, p. 155 - 167

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Citation Number: 33

Abstract

Abstract The macrocyclic pentolide 1, hexolide 2, and heptolide 3 constitute ca. 80% of the oligomers formed in ca. 50% yield from enantiomerically pure 3-hydroxybutanoic acid under Yamaguchi's macrolactonization conditions. The FAB mass spectra of the MH+, M Na+, and MCs+ are reported (Figs. 2, 3, 5, and 6). No cyclic tetramer is detected. The 1 H-NMR spectra of the cyclic oligomers, of the monomer, and of the polymer (PHB) are very similar ...