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

5 years ago

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

Chieko Ino, Tatsuya Shirahata, Yoshinori Kobayashi, Kazuo Kamaike, Hiroaki Miyaoka, Tomoki Miyata, Takafumi Yoshikawa, Fumi Mizuno, Ikuma Yamazaki, Masao Hirotani, Yoshihisa Asada, Koichiro Ota, Mei Fukui, Takahiro Saigoku

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).

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b02141

DOI: 10.1021/acs.joc.7b02141