Mandal Tirtha, Karmakar Shilpi, Kapat Ajoy, Dash Jyotirmayee
School of Chemical Sciences, Indian Association for the Cultivation of Science, Jadavpur, Kolkata 700032, India.
ACS Omega. 2021 Oct 4;6(41):27062-27069. doi: 10.1021/acsomega.1c03629. eCollection 2021 Oct 19.
A modular and flexible three-step synthetic strategy has been developed for the synthesis of acridone natural products of biological significance. The tetracyclic core of acridone derivatives has been achieved efficiently in high yield from commercially available anthranilic acid and phenol derivatives via condensation reaction, followed by regioselective annulation. Acridone alkaloids acronycine and noracronycine are synthesized in improved overall yields in fewer steps than the previously reported approaches. The method has further been used for the synthesis of atalaphyllidine and 5-hydroxynoracronycine in excellent yields for the first time. Moreover, the synthetic utility of the present strategy has been showcased by the synthesis of oxa and thia analogues of acronycine alkaloid.
已开发出一种模块化且灵活的三步合成策略，用于合成具有生物学意义的吖啶酮天然产物。通过缩合反应，从市售邻氨基苯甲酸和苯酚衍生物高效地以高收率获得了吖啶酮衍生物的四环核心，随后进行区域选择性环合。与先前报道的方法相比，吖啶酮生物碱丙烯吖啶和去甲丙烯吖啶的合成步骤更少，总收率更高。该方法首次进一步用于以优异的收率合成阿他叶啶和5-羟基去甲丙烯吖啶。此外，通过合成丙烯吖啶生物碱的氧杂和硫杂类似物，展示了本策略的合成实用性。
