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

文献情報

出版日 2020-01-14

DOI 10.1039/C9OB02490E

インパクトファクター 3.876

著者

Ji-Qin Hou, Jiang-Hong Yu, Heng Zhao, Ying-Ying Dong, Qiu-Shi Peng, Bao-Bao Zhang, Hao Wang

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要旨

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.

掲載誌

Organic & Biomolecular Chemistry

CiteScore: 3.4

自己引用率: 10.3%

年間論文数: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

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

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