Total synthesis of (±) commiphoranes C-D and their epimers

Xiaoyu Liu; Haidong Deng; Yingjun Jiang; Yang Cao; Zhe Wang; Xiaozhen Jiao; Ping Xie

doi:10.1039/d2ob00158f

Total synthesis of (±) commiphoranes C-D and their epimers

Org Biomol Chem. 2022 Mar 9;20(10):2102-2108. doi: 10.1039/d2ob00158f.

Authors

Xiaoyu Liu¹, Haidong Deng², Yingjun Jiang¹, Yang Cao¹, Zhe Wang¹, Xiaozhen Jiao¹, Ping Xie¹

Affiliations

¹ State Key Laboratory of Bioactive Substance and Function of Natural Medicine, Beijing Key Laboratory of Active Substance Discovery and Druggability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China. jiaoxz@imm.ac.cn.
² Beijing Key Laboratory of New Drug Mechanisms and Pharmacological Evaluation Study, Department of Pharmacology, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, 100050, China.

PMID: 35195145
DOI: 10.1039/d2ob00158f

Abstract

(±) Commiphorane C, (±) commiphorane D, and their two isomers were synthesized through a linear synthesis strategy in 14 steps. Key features of the strategy include the construction of the relative configurations of C-5 and C-6 via aldehyde crotylation followed by the Mitsunobu reaction and ring A via an intramolecular Aldol reaction. The biological evaluation revealed that (±) commiphorane C and (±) isomer-1 significantly attenuated the overproduction of fibronectin, collagen I, and α-SMA in TGF-β1-induced rat renal proximal tubular cells. Intermediate (±) 11 significantly decrease the overexpression of collagen I. Cytotoxicity studies showed that 1a-1d and (±) 11 were not toxic to NRK-52E cells.

Publication types

Research Support, Non-U.S. Gov't