Total Syntheses of Lobaric Acid and Its Derivatives from the Antarctic Lichen Stereocaulon alpinum

The first total syntheses of the natural products lobaric acid (1) and its derivatives isolated from the Antarctic lichen Stereocaulon alpinum are reported in this study. Lobarin (3), with a pseudodepsidone structure, was synthesized first in 11 steps by utilizing an Ullmann aryl ether coupling reac...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2018-06, Vol.81 (6), p.1460-1467
Main Authors: Kim, Tai Kyoung, Kim, Joung Eun, Youn, Ui Joung, Han, Se Jong, Kim, Il-Chan, Cho, Cheon-Gyu, Yim, Joung Han
Format: Article
Language:English
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Summary:The first total syntheses of the natural products lobaric acid (1) and its derivatives isolated from the Antarctic lichen Stereocaulon alpinum are reported in this study. Lobarin (3), with a pseudodepsidone structure, was synthesized first in 11 steps by utilizing an Ullmann aryl ether coupling reaction, and lobaric acid was synthesized in an additional three steps by a seven-membered lactonization reaction. Various derivatives were also obtained from the prepared lobaric acid, and the synthetic compounds exhibited significant PTP1B inhibitory activities.
ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.8b00227