Furanomycin Analogs: Optically Active Norfuranomycins

A Convergent Approach to Cyclopeptide Alkaloids: Total Synthesis of Sanjoinine G1

“…The widespread occurrence of these 13-, 14-, and 15-membered macrocyclic molecules in different plants such as rhamnaceae, pendaceae, and rubiaceae has made them an important class of natural products. 1,2 Since the structure elucidation of pandamine (1, Figure 1) by Goutarel and Paı ¨s in 1964, 3 this family of natural product has grown rapidly and encompasses nowadays a group of over 200 compounds. Although they displayed various interesting biological activities, their limited availability from natural sources has hampered extensive pharmacological investigations.…”

Mucronine J, a 14-Membered Cyclopeptide Alkaloid from Zizyphus mucronata

“…General Experimental Procedures. 1 H-and 13 C-NMR spectra were recorded on a Bruker AC 300 spectrometer, equipped with an Aspect 3000 computer, at 300.13 MHz and 75.47 MHz, respectively, using CDCl 3 as solvent. The resonances of residual CHCl 3 at δ H 7.24 and δ C 77.0 were used as internal reference.…”

“…A voucher specimen is on deposit in the Table 1. 1 H (300 MHz) and 13 C NMR (75 MHz) Data for Mucronine J, 1 (CDCl3, 296 K) 1 H δ (m, J, Hz) 13 Amino Acid Analysis. Compound 1 (1 mg) was hydrolyzed with 8 N HCl (0.5 mL) in a sealed tube at 110 °C under N 2 for 24 h. After cooling, the residue was dried over potassium hydroxide pellets.…”

“…A solution conformation is proposed on the basis of NOE experiments in combination with MM2 calculations.Zizyphus mucronata Willd., a Rhamnaceae of central and southern Africa, is employed by the natives in the treatment of diarrhea, dysentery, and skin infections. 1 Previous chemical studies on the bark revealed cyclopeptide alkaloids of the mucronine family. [2][3][4][5][6][7] All were characterized by the presence of a styrylamine group in a 15-membered cyclopeptide alkaloid, except mucronine D, which is a 13-membered ring system.From the root bark, a new 14-membered cyclopeptide alkaloid (1) together with the known abyssenine A 6 and mucronine D 7 were isolated.…”

“…Zizyphus mucronata Willd., a Rhamnaceae of central and southern Africa, is employed by the natives in the treatment of diarrhea, dysentery, and skin infections. 1 Previous chemical studies on the bark revealed cyclopeptide alkaloids of the mucronine family. [2][3][4][5][6][7] All were characterized by the presence of a styrylamine group in a 15-membered cyclopeptide alkaloid, except mucronine D, which is a 13-membered ring system.…”