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. 2018 Jun 22;81(6):1460-1467.
doi: 10.1021/acs.jnatprod.8b00227. Epub 2018 Jun 7.

Total Syntheses of Lobaric Acid and Its Derivatives From the Antarctic Lichen Stereocaulon Alpinum

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Total Syntheses of Lobaric Acid and Its Derivatives From the Antarctic Lichen Stereocaulon Alpinum

Tai Kyoung Kim et al. J Nat Prod. .

Abstract

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.

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