Total Synthesis, structure revision and antifungal activity of palmarumycin B8 and B7.

ABSTRACT

Palmarymycins B8 (1), its regioisomer (2) and B7 (3) were synthesized via 10-, 9-, and 11-steps in 6.5 %, 2.3 % and 0.54 % overall yields from chroman-4-one (4), 4-hydroxyindanone (12), and 2,5-dimethoxybenzaldehyde (20) as the starting materials, using benzyl protection, enol trimethylsilyl ether by TMSOTf, Rubottom oxidation and deprotection with hydrogenation under Pd/C catalyst as the key steps, respectively. Their structures were characterized by 1H, 13C NMR, COSY, HSQC, HMBC and HR-ESI-MS spectral data. The structure of palmarumycin B8 was revised from 1 to 2 based on the total synthesis, 2D NMR analysis and DFT calculation. The antifungal assay results indicated that palmarumycin B8 (1) showed moderate inhibitory activity against Phytophthora capsica. Compounds 15 and 16 exhibited excellent in vitro antifungal activities against P. capsica with EC50 values of 2.17 and 8.50 µg/mL, respectively.