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

• 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

Synthesis of the B-seco limonoid core scaffold

• Hanna Bruss,
• Hannah Schuster,
• Rémi Martinez,
• Markus Kaiser,
• Andrey P. Antonchick and
• Herbert Waldmann

Beilstein J. Org. Chem. 2014, 10, 194–208, doi:10.3762/bjoc.10.15

• the developed strategy ended up failing in more complex and sterically demanding systems. Keywords: B-seco limonoids; biology oriented synthesis; Ireland–Claisen rearrangement; natural products; tetranortriterpenoids; Introduction B-seco limonoids are a family of more than 100 highly oxygenated

• plant tetranortriterpenoids derived from the 4,4,8-trimethyl-17-furanylsteroid core structure I (Figure 1) [1][2][3]. Members of this natural product class, like 21-hydroxytoonacilide (1) [4][5] and prieurianin (2) [6][7][8][9][10][11][12][13][14][15][16] display antifeedant [6][7][17][18][19][20][21