Alepric, Aleprylic, Aleprestic and Aleprolic Acids, New Homologs of Chaulmoogric Acid

New cyclopentenyl fatty acids in Flacourtiaceae. Straight-chain fatty acids and cycloic fatty acids in lipids during maturation of the seeds

“…The most prominent cyclopentenyl fatty acids are hydnocarpic acid, 11-(2-cyclopenten-l-yl)undecanoic acid, chaulmoogric acid, 13-(2-cyclopenten-l -yl)tridecanoic acid, and gorlic acid, a Qs-cyclopentenyl fatty acid having a double bond in 6 position of the aliphatic chain (Paget, 1937). In addition, several cyclopentenyl fatty acids of shorter chain lengths, aleprolic, aleprestic, aleprylic, and alepric acids, are known (Cole and Cardoso, 1939). The correct structure of the cyclopentenyl fatty acids has been established by Shriner and Adams (1925) and the first total synthesis of a naturally t From the Bundesanstalt für Fettforschung, Instituí für Technologie und Biochemie, .…”

Dynamic kinetic Asymmetric Transformations with Hard Nucleophiles: Cyclopentens for Antituberculosis and Antibiotic

“…Fletcher group [2] applied the method to short, straightforward, enantioselective syntheses of three natural products (Figure 1) which compare favorably to previously reported syntheses, and will facilitate the preparation of analogues, these acids have been first isolated from Hydnocarpus wightiana oil (chaulmoogric oil) by Cole and Cardoso [1] in 1939, this oil had been used in the East against leprosy and various skin conditions for many hundreds of years, and was the standard remedy [3,4] for leprosy.…”

“…These natural products have timely biological activity and the eventual synthesis of derivatives will help develop structure-activity relationships. Cyclopentene natural products Alepric acid [1], aleprestic acid [1], and gorlic acid [1], have not previously had their synthesis reported. The asymmetric addition reaction is a dynamic kinetic asymmetric transformation (DYKAT) to a racemic allylic chloride to give cyclopentenes with high level of ee [2].…”

The Cyclopentenyl Fatty Acids

“…Various tissues of Flacourtiaceae contain cyclic compounds of low molecular weights, such as deidaclin [10,59], cyclopentenylglycine [18,51], and aleprolic acid [14]. The structures of these cyclopentene derivatives are shown in Figure 8.…”