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Phellilane L, Sesquiterpene Metabolite of Phellinus linteus: Isolation, Structure Elucidation, and Asymmetric Total Synthesis

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posted on 01.11.2017, 00:00 by Koichiro Ota, Ikuma Yamazaki, Takahiro Saigoku, Mei Fukui, Tomoki Miyata, Kazuo Kamaike, Tatsuya Shirahata, Fumi Mizuno, Yoshihisa Asada, Masao Hirotani, Chieko Ino, Takafumi Yoshikawa, Yoshinori Kobayashi, Hiroaki Miyaoka
A new cyclopropane-containing sesquiterpenoid, phellilane L (1), was isolated from the medicinal mushroom Phellinus linteus (“Meshimakobu” in Japanese), a member of the Hymenochaetaceae family and a well-known fungus that is widely used in East Asia. The planar structure of 1 was determined on the basis of spectroscopic analysis. The authors achieved the first total synthesis of 1. Our protecting group-free synthesis features a highly stereoselective one-pot synthesis involving an intermolecular alkylation/cyclization/lactonization strategy for construction of the key cyclopropane-γ-lactone intermediate. Additionally, our synthesis determined the absolute configuration of phellilane L (1).