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...

Full description

Saved in:
Bibliographic Details
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
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
TRIMERS
Online AccessGet full text

Cover

More Information
Summary: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).
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c03120