Total Synthesis of Clavilactones

Takao, Ken Ichi; Mori, Keisuke; Kasuga, Kenya; Nanamiya, Ryuki; Namba, Ayumi; Fukushima, Yuuki; Nemoto, Ryuichi; Mogi, Takuma; Yasui, Hirofumi; Ogura, Atsushi; Yoshida, Keisuke; Tadano, Kin Ichi

doi:10.1021/acs.joc.7b03268

Cited by 19 publications

(10 citation statements)

References 47 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…251 The total synthesis process of the EGFR tyrosine kinase inhibitors, 244 , 245 , and 247 , as well as the revision of the structure of 247 , was reported by the Takao group. 252 Another new meroterpenoid analog, clavilactone F ( 249 ), was isolated from C. clavipes in 2019 by Sun et al , along with 244 and 247 . 253 They were evaluated for antiproliferative activities against human cancer cells HepG2 and A549, as well as against normal cell line GES-1; however, they did not show any significant activity ( 249 : IC 50 = 18.22–33.27 μM, 244 : IC 50 = 32.14 μM against HepG2, IC 50 >50 μM and >100 μM against A549 and GES-1, respectively, and 247 : IC 50 = 9.32 μM–38.13 μM).…”

Section: Non-peptide Secondary Metabolites From Poisonous Mushroomsmentioning

confidence: 99%

Non-peptide secondary metabolites from poisonous mushrooms: overview of chemistry, bioactivity, and biosynthesis

Lee

et al. 2022

Nat. Prod. Rep.

View full text Add to dashboard Cite

show abstract

Section: Non-peptide Secondary Metabolites From Poisonous Mushroomsmentioning

confidence: 99%

Non-peptide secondary metabolites from poisonous mushrooms: overview of chemistry, bioactivity, and biosynthesis

Lee

et al. 2022

Nat. Prod. Rep.

View full text Add to dashboard Cite

show abstract

“…The structures of clavilactones D and E (7), were initially inferred by 1-and 2-D NMR data [67]. However, the subsequent total synthesis of clavilactones A, B, and D led to a revision of the original structure of clavilactone D which was established to be as formula (8) in Figure 4 [68]. Clavilactone A, B, and D displayed potent inhibitory activity in kinase assays against the Ret/ptc1 and epidermal growth factor receptor (EGFR) tyrosine kinases [67,69].…”

Section: Ampulloclitocybe Clavipes (Pers) Redhead Lutzoni Moncalvomentioning

confidence: 99%

Bioactive Phytochemical Constituents of Wild Edible Mushrooms from Southeast Asia

et al. 2020

View full text Add to dashboard Cite

Mushrooms have a long history of uses for their medicinal and nutritional properties. They have been consumed by people for thousands of years. Edible mushrooms are collected in the wild or cultivated worldwide. Recently, mushroom extracts and their secondary metabolites have acquired considerable attention due to their biological effects, which include antioxidant, antimicrobial, anti-cancer, anti-inflammatory, anti-obesity, and immunomodulatory activities. Thus, in addition to phytochemists, nutritionists and consumers are now deeply interested in the phytochemical constituents of mushrooms, which provide beneficial effects to humans in terms of health promotion and reduction of disease-related risks. In recent years, scientific reports on the nutritional, phytochemical and pharmacological properties of mushroom have been overwhelming. However, the bioactive compounds and biological properties of wild edible mushrooms growing in Southeast Asian countries have been rarely described. In this review, the bioactive compounds isolated from 25 selected wild edible mushrooms growing in Southeast Asia have been reviewed, together with their biological activities. Phytoconstituents with antioxidant and antimicrobial activities have been highlighted. Several evidences indicate that mushrooms are good sources for natural antioxidants and antimicrobial agents

show abstract

“…[6c] In at otal synthesis of clavilactone A, Takao and coworkers strategically exploited ethylene to retrieve aproduct from its homocoupled state (Scheme 3). [7] Zhenxing Liu was born in Dengzhou, China. He received his undergraduate degree at Zhengzhou University in 2011.…”

Section: Fori Mproving Efficiencymentioning

confidence: 99%

Impact of Ethylene on Efficiency and Stereocontrol in Olefin Metathesis: When to Add It, When to Remove It, and When to Avoid It

et al. 2020

View full text Add to dashboard Cite

Ethylene is the byproduct of olefin metathesis reactions that involve one or more terminal alkenes. Its volatility is one reason why many cross‐metathesis or ring‐closing metathesis processes, which are reversible transformations, are efficient. However, because ethylene can be converted to a methylidene complex, which is a highly reactive but relatively unstable species, its concentration can impact olefin metathesis in other ways. In some cases, introducing excess ethylene can increase reaction rate owing to faster catalyst initiation. Ethylene and a derived methylidene complex can also advantageously inhibit substrate or product homocoupling, and/or divert a less selective pathway. In other instances, a methylidene's low stability and high activity may lead to erosion of efficiency and/or kinetic selectivity, making it preferable that ethylene is removed while being generated. If methylidene decomposition is so fast that there is little or no product formation, it is best that ethylene and methylidene complex formation is avoided altogether. This is accomplished by the use of di‐ or trisubstituted alkenes in stereoretentive processes, which includes adopting methylene capping strategy. Here, we analyze the different scenarios through which ethylene and the involvement of methylidene complexes can be manipulated and managed so that an olefin metathesis reaction may occur more efficiently and/or more stereoselectively.

show abstract

Total Synthesis of Clavilactones

Cited by 19 publications

References 47 publications

Non-peptide secondary metabolites from poisonous mushrooms: overview of chemistry, bioactivity, and biosynthesis

Non-peptide secondary metabolites from poisonous mushrooms: overview of chemistry, bioactivity, and biosynthesis

Bioactive Phytochemical Constituents of Wild Edible Mushrooms from Southeast Asia

Impact of Ethylene on Efficiency and Stereocontrol in Olefin Metathesis: When to Add It, When to Remove It, and When to Avoid It

Contact Info

Product

Resources

About