Studies on the syntheses of sesquiterpene lactones. 11. The syntheses of 3-epizaluzanin C, zaluzanin C, zaluzanin D, and related compounds 3.alpha.-hydroxyguaia-1(10),4(15),11(13)-trieno-12,6.alpha.-lactone and 3.alpha.-hydroxyguaia-4(15),9,11(13)-trieno-12,6.alpha.-lactone

Guaianolides as Immunomodulators. Synthesis and Biological Activities of Dehydrocostus Lactone, Mokko Lactone, Eremanthin, and Their Derivatives

“…(11S)-1,1-(Ethylenedioxy)eudesm-3-eno-13,6R-lactone (7). A mixture of 6 (2.30 g, 9.26 mmol), ethylene glycol (137 mL), and TsOH‚H2O (305 mg, 1.60 mmol) in dry benzene (500 mL) was refluxed in a flask equipped with a Dean-Stark column packed with molecular sieves for 24 h, and then benzene was removed.…”

“…The guaianolides represent one of the largest groups of sesquiterpene lactones covering over 500 known naturally occurring compounds . Some of these compounds have been reported to possess high antitumor, − antishistosomal, , anthelmintic, contraceptive, root-growth stimulatory, , root-growth and germination inhibitory activities, and antiulcer activity. , This diverse bioactivity of guaianolides makes them attractive synthetic targets since the availability of these compounds from natural sources is very limited. It is important to make these natural products available in substantial quantities to explore in detail their bioactivities.…”

Studies on the Synthesis of Sesquiterpene Lactones, 16. The Syntheses of 11β,13-Dihydrokauniolide, Estafiatin, Isodehydrocostuslactone, 2-Oxodesoxyligustrin, Arborescin, 1,10-Epiarborescin, 11β,13-Dihydroludartin, 8-Deoxy-11β,13-dihydrorupicolin B, 8-Deoxyrupicolin B, 3,4-Epiludartin, Ludartin, Kauniolide, Dehydroleucodin, and Leucodin

“…5 Hz, H-14), 5.57 (1H, d,7=3.1 Hz, H-13), 6.14 (1H, m, Wbl2=4. 5 Hz, H-3), 6.28 (1H, d, 7=3.5 Hz, H-13); 13Cnmrb 19.93 (q), 31.16 (t), 36.48 (t), 46.11(d), 53.19(d), 56.13(d), 83.30(d), 117.29 (t) , 121.21 (t), 132.60 (d), 138.36 (s), 144.10 (s), 169.42 (s), 177.72 (s), 206.65 (115)-2-Oxoguala-3,10( 1 4)-dieno 12,6a-LACTONE [12].-Into a solution of 3 (54 mg, 0.23 mmol) in a mixture of CC14 (2.2 ml), AczO (0.16 ml, 1.66 mmol) and AcOH (3.30 ml), was added 1.79 M f-butyl chromate (0.90 ml, 1.61 mmol) in CC14 under stirring. The solution was stirred for 3 hat room temperature and aqueous oxalic acid (38 mg, 0.42 mmol/2.1 ml H20) was added.…”

Constituents of Laurus nobilis L. inhibit recombinant human lanosterol synthase

“…Fraction 1 was further separated by silica gel column chromatography using ether-hexane, followed by HPLC (80% MeOH) , and yielded eremanthine (5, 4.1 mg) [10], dehydrocostus lactone (6, 8.6 mg) [11] and costunolide (7, 8.1 mg) [12]. Fraction 2 was further separated by silica gel column chromatography using ether-hexane, followed by HPLC (80% MeOH), and yielded zaluzanin C (8, 31.7 mg) [13], zaluzanin D (9, 10.3 mg) [14], and reynosin (10, 5.1 mg) [15]. These compounds were identified by comparison of their spectral data with those published (Figs.…”