Microbial metabolites part 11 total synthesis and absolute configuration of s carlosic acid 4 butyryl 2 5 dihydro 3 hydroxy 5 oxo furan 2 acetic acid and conversion of r 5 methyl tetronic acid into r carolic acid 3 4 di hydro 8 methyl furo 3 4 b oxepin 5 2h 8h dione

Bloomer, J.L.; Kappler, F.E.

Journal of the Chemical Society Perkin Transactions I 14: 1485-1491


Accession: 005896634

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Synthesis of (S)-2,5-dihydro-3-hydroxy-5-oxofuran-2-acetic acid and its methyl ester were described. Biomimetic acylations of the ester and of (R)-3-hydroxy-2-methylfuran-2(5H)-one[R)-.gamma.-methyltetronic acid] to produce (S)-carlosic acid and (R)-carolic acid, respectively, are described. The absolute configuration of carlosic acid from Penicillium charlesii NRRL 1887 was established as S.