Brønsted Acid-Mediated Conversion of Naturally Abundant Lathyrane Diterpenes: Are Rare 10,11- seco-Lathyrane Diterpenes Artifacts?

  • J Nat Prod. 2024 Jan 26;87(1):113-120. doi: 10.1021/acs.jnatprod.3c00652.
Wei Cheng  1  2 ,  Wan-Sheng Ji  1 ,  Yu Li  1 ,  Xiaohuan Li  1 ,  Feng-Zheng Chen  3 ,  Jin-Bu Xu  1  4 ,  Feng Gao  1  2  4
Affiliations
  • 1. Sichuan Engineering Research Center for Biomimetic Synthesis of Natural Drugs, School of Life Science and Engineering, Southwest Jiaotong University, Chengdu 610031, Sichuan, People's Republic of China.
  • 2. Key Laboratory of Advanced Technologies of Material, Minister of Education, School of Materials Science and Engineering, Southwest Jiaotong University, Chengdu 610031, Sichuan, People's Republic of China.
  • 3. College of Chemistry, Leshan Normal University, Leshan 614004, Sichuan, People's Republic of China.
  • 4. Yibin Institute of Southwest Jiaotong University, Yibin 644000, Sichuan, People's Republic of China.
PMID: 38095929 DOI: 10.1021/acs.jnatprod.3c00652
Abstract

The question of whether rare 10,11-seco-lathyranes are natural products or artifacts is thoughtfully considered after a Brønsted acid-mediated chemical conversion of naturally abundant 5/11/3 lathyrane type diterpenes into 10,11-seco-lathyranes was developed. Benefiting from this concise route, a series of 10,11-seco-lathyrane products (1-14) were smoothly synthesized. The conversion may involve an acid promoted cyclopropane ring opening accompanied by a double bond shift with final trapping of carbocation. The ease of this chemical conversion under mildly acidic conditions may imply that the 10,11-seco-lathyranes isolated to date are artifacts. This work not only develops a new modular synthetic strategy for efficient constructing rare 10,11-seco-lathyranes, but also provides a promising bioactive diterpene with excellent effect against the NO production on LPS-induced BV-2 cells.