Mesima, Sanghwang · 2017 · Journal Article
High relevancePhellilane L, Sesquiterpene Metabolite of Phellinus linteus: Isolation, Structure Elucidation, and Asymmetric Total Synthesis.
Phellinus linteus
Key points
- 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)
Metadata-grounded summary
Citation abstract
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).
Citation
Ota K, Yamazaki I, Saigoku T, Fukui M, Miyata T, Kamaike K, et al. (2017). Phellilane L, Sesquiterpene Metabolite of Phellinus linteus: Isolation, Structure Elucidation, and Asymmetric Total Synthesis. The Journal of organic chemistry https://doi.org/10.1021/acs.joc.7b02141 PMID: 29090580
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