A convergent synthetic approach to the tetracyclic core framework of khayanolide-type limonoids

• Zhiyang Zhang,
• Jialei Hu,
• Hanfeng Ding,
• Li Zhang and
• Peirong Rao

Beilstein J. Org. Chem. 2025, 21, 926–934, doi:10.3762/bjoc.21.75

• , Hangzhou 310018, Zhejiang, China 10.3762/bjoc.21.75 Abstract A convergent approach for the enantioselective construction of an advanced intermediate containing the [5,5,6,6]-tetracyclic core framework of the khayanolide-type limonoids was described. The strategy features an acylative kinetic resolution of

• the benzylic alcohol, a 1,2-Grignard addition and an AcOH-interrupted Nazarov cyclization. Keywords: enantioselective synthesis; interrupted Nazarov cyclization; khayanolide-type limonoids; tetracyclic framework; Introduction Limonoids, a class of tetranortriterpenoids derived biosynthetically from

• . A preliminary investigation revealed that krishnolide A (7) exhibited unique anti-human immunodeficiency virus (HIV) activity, representing the first report of anti-HIV activity in khayanolide-type limonoids. However, the highly oxygenated and polycyclic scaffolds pose substantial challenges toward