Biomimetic Synthesis of Lavandiolides H, I, and K and Artematrolide F via Diels–Alder Reaction

The biomimetic synthesis of guaianolide dimers lavandiolides H, I, and K and artematrolide F containing a spirolactone moiety has been accomplished for the first time from naturally abundant arglabin in four to six steps with an overall yield up to 60%, and a series of natural product-like guaianoli...

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Published inOrganic letters Vol. 23; no. 21; pp. 8380 - 8384
Main Authors Li, Tian-Ze, Yang, Xiao-Tong, Wang, Jin-Ping, Geng, Chang-An, Ma, Yun-Bao, Su, Li-Hua, Zhang, Xue-Mei, Chen, Ji-Jun
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.11.2021
Amer Chemical Soc
Subjects
biomimetic synthesis
Chemistry
Chemistry, Organic
cycloaddition reactions
cytotoxicity
moieties
Physical Sciences
Science & Technology
TRIMERS
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Abstract The biomimetic synthesis of guaianolide dimers lavandiolides H, I, and K and artematrolide F containing a spirolactone moiety has been accomplished for the first time from naturally abundant arglabin in four to six steps with an overall yield up to 60%, and a series of natural product-like guaianolide dimers, trimer, and tetramer were also successfully synthesized. Notably, the trimeric compound exhibited antihepatoma cytotoxicity more potent than that of sorafenib with IC50 values of 6.2 μM (HepG2), 6.8 μM (Huh7), and 7.2 μM (SK-HEP-1).
AbstractList The biomimetic synthesis of guaianolide dimers lavandiolides H, I, and K and artematrolide F containing a spirolactone moiety has been accomplished for the first time from naturally abundant arglabin in four to six steps with an overall yield up to 60%, and a series of natural product-like guaianolide dimers, trimer, and tetramer were also successfully synthesized. Notably, the trimeric compound exhibited antihepatoma cytotoxicity more potent than that of sorafenib with IC50 values of 6.2 μM (HepG2), 6.8 μM (Huh7), and 7.2 μM (SK-HEP-1).
The biomimetic synthesis of guaianolide dimers lavandiolides H, I, and K and artematrolide F containing a spirolactone moiety has been accomplished for the first time from naturally abundant arglabin in four to six steps with an overall yield up to 60%, and a series of natural product-like guaianolide dimers, trimer, and tetramer were also successfully synthesized. Notably, the trimeric compound exhibited antihepatoma cytotoxicity more potent than that of sorafenib with IC values of 6.2 μM (HepG2), 6.8 μM (Huh7), and 7.2 μM (SK-HEP-1).
The biomimetic synthesis of guaianolide dialers lavandiolides H, I, and K and artematrolide F containing a spirolactone moiety has been accomplished for the first time from naturally abundant arglabin in four to six steps with an overall yield up to 60%, and a series of natural product-like guaianolide dimers, trimer, and tetramer were also successfully synthesized. Notably, the trimeric compound exhibited antihepatoma cytotoxicity more potent than that of sorafenib with IC50 values of 6.2 mu M (HepG2), 6.8 mu M (Huh7), and 7.2 mu M (SK-HEP-1).
The biomimetic synthesis of guaianolide dimers lavandiolides H, I, and K and artematrolide F containing a spirolactone moiety has been accomplished for the first time from naturally abundant arglabin in four to six steps with an overall yield up to 60%, and a series of natural product-like guaianolide dimers, trimer, and tetramer were also successfully synthesized. Notably, the trimeric compound exhibited antihepatoma cytotoxicity more potent than that of sorafenib with IC₅₀ values of 6.2 μM (HepG2), 6.8 μM (Huh7), and 7.2 μM (SK-HEP-1).
The biomimetic synthesis of guaianolide dimers lavandiolides H, I, and K and artematrolide F containing a spirolactone moiety has been accomplished for the first time from naturally abundant arglabin in four to six steps with an overall yield up to 60%, and a series of natural product-like guaianolide dimers, trimer, and tetramer were also successfully synthesized. Notably, the trimeric compound exhibited antihepatoma cytotoxicity more potent than that of sorafenib with IC50 values of 6.2 μM (HepG2), 6.8 μM (Huh7), and 7.2 μM (SK-HEP-1).The biomimetic synthesis of guaianolide dimers lavandiolides H, I, and K and artematrolide F containing a spirolactone moiety has been accomplished for the first time from naturally abundant arglabin in four to six steps with an overall yield up to 60%, and a series of natural product-like guaianolide dimers, trimer, and tetramer were also successfully synthesized. Notably, the trimeric compound exhibited antihepatoma cytotoxicity more potent than that of sorafenib with IC50 values of 6.2 μM (HepG2), 6.8 μM (Huh7), and 7.2 μM (SK-HEP-1).
Author Chen, Ji-Jun
Zhang, Xue-Mei
Wang, Jin-Ping
Yang, Xiao-Tong
Geng, Chang-An
Su, Li-Hua
Ma, Yun-Bao
Li, Tian-Ze
AuthorAffiliation State Key Laboratory of Phytochemistry and Plant Resources in West China and Yunnan Key Laboratory of Natural Medicinal Chemistry
University of Chinese Academy of Sciences
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Snippet The biomimetic synthesis of guaianolide dimers lavandiolides H, I, and K and artematrolide F containing a spirolactone moiety has been accomplished for the...
The biomimetic synthesis of guaianolide dialers lavandiolides H, I, and K and artematrolide F containing a spirolactone moiety has been accomplished for the...
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SubjectTerms biomimetic synthesis
Chemistry
Chemistry, Organic
cycloaddition reactions
cytotoxicity
moieties
Physical Sciences
Science & Technology
Title Biomimetic Synthesis of Lavandiolides H, I, and K and Artematrolide F via Diels–Alder Reaction
URI http://dx.doi.org/10.1021/acs.orglett.1c03120
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https://www.ncbi.nlm.nih.gov/pubmed/34634203
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Volume 23
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