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Biomimetic total syntheses of baefrutones A–D, baeckenon B, and frutescones A, D–F

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Abstract

Biomimetic total syntheses of baefrutones A–D (1–4), baeckenon B (5), and frutescones A, D–F (6–9), isolated from the leaves of Baeckea frutescens, were achieved in 9, 8, and 5 steps, respectively, in moderate to good yields (72–83%). The synthetic routes feature the Michael addition, oxidative [4 + 2] cycloaddition, and water-promoted Diels–Alder click reactions as the key steps. This study helped gain thorough mechanistic insights into the biosynthetic origins and provided a facile approach for the construction of a library of natural tasmanone-based meroterpenoid analogues. Moreover, compounds 1–9 show potent inhibitory effects against S. paratyphi and/or C. albicans with MIC values of 3.125–25 μg mL−1, and they could be promising lead molecules for the design of new antibiotic agents.

Graphical abstract: Biomimetic total syntheses of baefrutones A–D, baeckenon B, and frutescones A, D–F

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Article information


Submitted
19 Nov 2019
Accepted
09 Jan 2020
First published
14 Jan 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Paper

Biomimetic total syntheses of baefrutones A–D, baeckenon B, and frutescones A, D–F

J. Hou, J. Yu, H. Zhao, Y. Dong, Q. Peng, B. Zhang and H. Wang, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/C9OB02490E

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