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Discovery and Biomimetic Synthesis of a Phloroglucinol‐Terpene Adduct Collection from Baeckea frutescens and Its Biogenetic Origin Insight
Author(s) -
Luo ShiLin,
Hu LiJun,
Huang XiaoJun,
Su JunCheng,
Shao XueHua,
Wang Lei,
Xu HanHong,
Li ChuangChuang,
Wang Ying,
Ye WenCai
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202001111
Subject(s) - phloroglucinol , adduct , terpene , chemistry , quinone methide , cycloaddition , organic chemistry , stereochemistry , quinone , catalysis
A phloroglucinol‐terpene adduct (PTA) collection consisting of twenty‐four molecules featuring three skeletons was discovered from Baeckea frutescens . Inspired by its biosynthetic hypothesis, we synthesized this PTA collection by reductive activation of stable phloroglucinol precursors into highly reactive ortho ‐quinone methide ( o ‐QM) intermediates and subsequently Diels–Alder cycloaddition. We also demonstrated, for the first time, the generation process of the active o ‐QM by performing dynamic NMR and HPLC‐MS monitoring experiments. Moreover, the PTA collection showed significant antifeedant effect toward the Plutella xylostella larvae.