Issue 1, 2024

Isoxerophilins A and B, two diterpene heterodimers from Isodon xerophilus: structural elucidation and semisynthesis of isoxerophilin analogues

Abstract

Two types of novel diterpene heterodimers, isoxerophilins A (1, ent-kaurane–sempervirane) and B (2, ent-kaurane–abietane), were isolated from the roots of Isodon xerophilus. Their structures and absolute configurations were determined by spectroscopic data and single crystal X-ray diffraction analysis. A bioinspired semisynthesis of ten isoxerophilin analogues, featuring a tandem oxidative dearomatization/intermolecular Diels–Alder reaction, has been achieved, and the transformation of ferruginol into a sempervirane scaffold was accomplished by the SIBX-mediated tandem reaction. Compound 12 promotes MICA/B expression on SMMC-7721 cells.

Graphical abstract: Isoxerophilins A and B, two diterpene heterodimers from Isodon xerophilus: structural elucidation and semisynthesis of isoxerophilin analogues

Supplementary files

Article information

Article type
Research Article
Submitted
12 Dit 2023
Accepted
04 Xim 2023
First published
07 Xim 2023

Org. Chem. Front., 2024,11, 37-46

Isoxerophilins A and B, two diterpene heterodimers from Isodon xerophilus: structural elucidation and semisynthesis of isoxerophilin analogues

J. Dai, B. Yan, L. Kong, K. Hu, X. Li, X. Li, H. Sun, Y. Li and P. Puno, Org. Chem. Front., 2024, 11, 37 DOI: 10.1039/D3QO01679J

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