Discovery and Biomimetic Synthesis of a Polycyclic Polymethylated Phloroglucinol Collection from Rhodomyrtus tomentosa

Inspired by a previously reported biomimetic synthesis study, four new naturally occurring phloroglucinol trimers 1–4 with unusual 6/5/5/6/6/6-fused hexacyclic ring systems, along with two known analogues (5 and 6) and two known biogenetically related dimers (10 and 11), were isolated from Rhodomyrt...

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Published in:Journal of organic chemistry 2022-04, Vol.87 (7), p.4788-4800
Main Authors: Deng, Lu-Ming, Tang, Wei, Wang, Shu-Qin, Song, Jian-Guo, Huang, Xiao-Jun, Zhu, Hao-Yue, Li, Yao-Lan, Ye, Wen-Cai, Hu, Li-Jun, Wang, Ying
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Language:English
Subjects:
Biomimetics
Circular Dichroism
Molecular Structure
Myrtaceae - chemistry
Phloroglucinol - chemistry
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cited_by cdi_FETCH-LOGICAL-a248t-388613cde81d1b296a05a0089e486d24e73412223a5929c71760566a02dcc8923
cites cdi_FETCH-LOGICAL-a248t-388613cde81d1b296a05a0089e486d24e73412223a5929c71760566a02dcc8923
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container_issue 7
container_start_page 4788
container_title Journal of organic chemistry
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creator Deng, Lu-Ming
Tang, Wei
Wang, Shu-Qin
Song, Jian-Guo
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Ye, Wen-Cai
Hu, Li-Jun
Wang, Ying
description Inspired by a previously reported biomimetic synthesis study, four new naturally occurring phloroglucinol trimers 1–4 with unusual 6/5/5/6/6/6-fused hexacyclic ring systems, along with two known analogues (5 and 6) and two known biogenetically related dimers (10 and 11), were isolated from Rhodomyrtus tomentosa. Their structures and absolute configurations were unambiguously elucidated by spectroscopic analysis, X-ray diffraction, and electronic circular dichroism calculation. By mimicking two potentially alternative biosynthetic pathways, the first asymmetric syntheses of 1–4 and the racemic syntheses of 5 and 6 were achieved in only five to six steps without the need for protecting groups. Furthermore, phloroglucinol dimers 10 and 11 exhibited significant in vitro antiviral activity against the respiratory syncytial virus.
doi_str_mv 10.1021/acs.joc.2c00071
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source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects Biomimetics
Circular Dichroism
Molecular Structure
Myrtaceae - chemistry
Phloroglucinol - chemistry
title Discovery and Biomimetic Synthesis of a Polycyclic Polymethylated Phloroglucinol Collection from Rhodomyrtus tomentosa
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