Total Synthesis of (±)-Calanolide A and Its Anti-HIV Activity

Anti-HIV agent (±)-calanolide A has been synthesized by a four-step approach startingfrom phloroglucinol, including the Pechmann reaction, Friedel-Crafts acylation, cyclization,chromenylation and Luche reduction.

N-Oxide heterocycles and imidazoles replacing ring D of calanolides against Mycobacterium tuberculosis

We have explored the chemistry of N-oxide heterocycles and imidazoles replacing ring D of the natural product（＋）-calanolide A, and have synthesized 12 new analogues, two of which were active against both R Mtb and NR Mtb with MIC values of 12.5 mg/m L, which would lead to further optimization for more potent anti-TB candidates.

(±)-F18对映异构体的HPLC手性分离、绝对构型确定以及抗HIV-1活性研究

消旋(±)-F18(10-chloromethyl-11-demethyl-12-oxo-calanolide A)是对天然产物(+)-calanolide A进行结构优化得到的四环香豆素类非核苷类逆转录酶抑制剂。本文建立了高效液相色谱法手性分离(±)-F18对映异构体的方法,并制备得到两个光学异构体(R)-F18和(S)-F18。应用电子圆二色谱技术和量化计算方法确定了二者光学异构体的绝对构型。抗HIV-1活性筛选表明,(S)-F18和(R)-F18对17个NNRTI耐药病毒株有相似的耐药谱,但二者的抗病毒活性有显著的区别。其中(R)-F18对野生型病毒株、K101E和P225H耐药株抗病毒活性较(S)-F18高近10倍。