Total synthesis of cynaropicrin

Tenma Nakamura; Dinda B. Pitna; Kogaku Kimura; Yukiko Yoshimoto; Tomoya Uchiyama; Takaya Mori; Ryosuke Kondo; Shihori Hara; Yuki Egoshi; Shoya Yamaguchi; Noriyuki Suzuki; Yumiko Suzuki; Toyonobu Usuki

doi:10.1039/D1OB00657F

Total synthesis of cynaropicrin†

Tenma Nakamura,^a Dinda B. Pitna,^a Kogaku Kimura,^a Yukiko Yoshimoto,^a Tomoya Uchiyama,^a Takaya Mori,^a Ryosuke Kondo,^a Shihori Hara,^a Yuki Egoshi,^a Shoya Yamaguchi,^a Noriyuki Suzuki,^a Yumiko Suzuki

^a and Toyonobu Usuki

*^a

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* Corresponding authors

^a Department of Materials and Life Sciences, Faculty of Science and Technology, Sophia University, 7-1 Kioicho, Chiyoda-ku, Tokyo 102-8554, Japan
E-mail: t-usuki@sophia.ac.jp

Abstract

Cynaropicrin is found in artichoke (Cynara scolymus) and is the source of its bitter taste and it is a sesquiterpene lactone with a 5-7-5 tricyclic skeleton, six chiral centers, and four exo-olefins. This natural product has numerous attractive biological activities including the inhibition of NF-κB activation, antihepatitis C activity, and antitrypanosomal activity. In this study, the first total synthesis of cynaropicrin was achieved starting from (S)-α-pinene. The synthesis involved a stereoselective Favorskii rearrangement and an indium-promoted diastereoselective Barbier reaction.

This article is part of the themed collection: Total synthesis in OBC

Organic & Biomolecular Chemistry

Total synthesis of cynaropicrin†

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Total synthesis of cynaropicrin

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