Structure and Stereochemistry of Phaseolinic Acid: A New Acid from Macrophomina phaseolina

A new 16-membered tetraene macrolide JBIR-100 from a newly identified Streptomyces species

“…The structures 230-232 are very simple and butanolides in general are rather common natural products, however, simple 2,3-or 2,4-dialkylated butanolides have not often been described from bacteria, and also from fungi, very few related butanolides are known. The various protolichesterinic acids, phaseolinic acid, [338] nephrosteranic acid [339] and a few other long-chain butanolides from lichens and some fungi, are having the closest similarity with 230-232; they carry, however, an additional carboxy group at C3. Among the less than 20 related plant products, some are showing a surprising similarity with 230-232: in the murrayacoumarins or the 6,7-dihydroclauslactones, butanolides of type 230-232 are connected with a coumarine system via an ether bond [340,341] .…”

Synthesis of (±)-Nephromopsinic, (−)-Phaseolinic, and (−)-Dihydropertusaric Acids

“…Efficient methods for the preparation of b,g-trans-gbutyrolactones have been reported, and a few syntheses of enantiomerically pure material have appeared (for leading references, see [4 ± 10]). However, b,g-cis disubstituted systems such as (À)-nephromopsinic acid (1) [11 ± 13], (À)-dihydropertusaric acid (2) [14 ± 16], and (À)-phaseolinic acid (3) [17] are more difficult to prepare. Interestingly, these three compounds possess a very similar substitution pattern, they differ only by the C residue in the g-position.…”

Chemo-Enzymatic Synthesis and Determination of the Absolute Configuration of Both Enantiomers of Methyl trans-5-Oxo-2-pentylpyrrolidine-3-carboxylate Precursors of the Aza Analogues of (+)- and (−)-Methylenolactocin

“…Examples are (À)-methylenolactocin (4) [8], which possesses antitumor and antibiotic activity, (À)-protolichesterinic acid (5) [8a,c] [9], an antitumor, antibacterial, and growth-regulating compound, and (À)-phaseolinic acid (6) [8b] [10], a metabolite of the fungus, Macrophomina phaseolina. Several asymmetric syntheses of these polyfunctionalized lactones have been reported in the literature [11], a few based on a chemo-enzymatic approach, e.g., the synthesis of a precursor of (À)-4 [12] and both enantiomers of 6 [10].…”

“…IR (nujol): 3238 (COOH), 1715 (COOH), 1650 (NCO). 1 H-NMR :10.02 (br. s, COOH); 7.59 (s, NH); 3.83 (m, HÀC(2)); 2.85 (m, HÀC(3)); 2.72 (dd, J 17.1, 7.3, HÀC(4)); 2.59 (dd, J 17.1, 9.8, HÀC(4)); 1.64 ± 1.43 (m, CH 2 (CH 2 ) 3 Me), 1.30 ± 1.20 (m, CH 2 (CH 2 ) 3 Me); 0.80 (br.…”

“…IR (nujol): 3238 (COOH), 1715 (COOH), 1650 (NCO). 1 H-NMR:10.80 (br. s, COOH); 7.73 (s, NH); 3.90 (m, HÀC…”