Full Stereochemical Assignment and Synthesis of the Potent Anthelmintic Pyrrolobenzoxazine Natural Product CJ-12662

Didier, Charles; Critcher, Douglas J.; Walshe, Nigel; Kojima, Yasuhiro; Yamauchi, Yuji; Barrett, Anthony G. M.

doi:10.1021/jo048711t

Cited by 48 publications

(39 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Compound 8 , named (1 S ,2 R ,4a R ,5 R ,8 R ,8a R )-1,8a-dihydroxy-2-acetoxy- 3,8-dimethyl-5-(prop-1-en-2-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene, was previously obtained as the degradation product of the natural product CJ-12662, which was obtained from the fermentation broth of Aspergillus fischeri var. thermomutatus ATCC 18,618 [ 19 ] and later also isolated from fungi Neosartorya pseudofischeri and Eurotium chevalieri [ 20 , 21 ]. However, the single-crystal X-ray diffraction data were never reported.…”

Section: Resultsmentioning

confidence: 99%

Five New Cytotoxic Metabolites from the Marine Fungus Neosartorya pseudofischeri

Lan

et al. 2016

Marine Drugs

View full text Add to dashboard Cite

The marine fungus Neosartorya pseudofischeri was isolated from Acanthaster planci from the South China Sea. In a preliminary bioactivity screening, the crude methanol extract of the fungal mycelia showed significant inhibitory activity against the Sf9 cell line from the fall armyworm Spodoptera frugiperda. Five novel compounds, including 5-olefin phenylpyropene A (1), 13-dehydroxylpyripyropene A (4), deacetylsesquiterpene (7), 5-formyl-6-hydroxy-8-isopropyl-2- naphthoic acid (9) and 6,8-dihydroxy-3-((1E,3E)-penta-1,3-dien-1-yl)isochroman-1-one (10), together with eleven known compounds, phenylpyropene A (2) and C (3), pyripyropene A (5), 7-deacetylpyripyropene A (6), (1S,2R,4aR,5R,8R,8aR)-1,8a-dihydroxy-2-acetoxy-3,8-dimethyl-5- (prop-1-en-2-yl)-1,2,4a, 5,6,7,8,8a-octahydronaphthalene (8), isochaetominine C (11), trichodermamide A (12), indolyl-3-acetic acid methyl ester (13), 1-acetyl-β-carboline (14), 1,2,3,4-tetrahydro-6-hydroxyl-2-methyl-l,3,4-trioxopyrazino[l,2-a]-indole (15) and fumiquinazoline F (16), were obtained. The structures of these compounds were determined mainly by MS and NMR data. The absolute configuration of 9 was assigned by the single-crystal X-ray diffraction studies. Compounds 1–11 and 15 showed significant cytotoxicity against the Sf9 cells from S. frugiperda.

show abstract

Section: Resultsmentioning

confidence: 99%

Five New Cytotoxic Metabolites from the Marine Fungus Neosartorya pseudofischeri

Lan

et al. 2016

Marine Drugs

View full text Add to dashboard Cite

show abstract

“…Barrett and co-workers enantioselectively prepared the 7-chloro-1-methyltryptophan derivative 28 from 1-chloro-2-nitrobenzene by BIS (Scheme 17), 95 and used 26 as the key intermediate in a four-step synthesis of CJ-12662, (Fig. 1) a potent anthelmintic natural product from the fermentation broth of Aspergillus fischeri var.…”

Section: Syntheses From 7-haloindolesmentioning

confidence: 99%

Applications of Bartoli indole synthesis

2014

View full text Add to dashboard Cite

In 1989, the reaction of vinyl magnesium halides with ortho-substituted nitroarenes leading to indoles was discovered. This reaction is now frequently reported as the "Bartoli reaction" or the "Bartoli indole synthesis" (BIS). It has rapidly become the shortest and most flexible route to 7-substituted indoles, because the classical indole syntheses generally fail in their preparation. The flexibility of the Bartoli reaction is great as it can be extended to heteroaromatic nitro derivatives and can be run on solid support. This review will focus on the use of the Bartoli indole synthesis as the key step in preparations of complex indoles, which appeared in the literature in the last few years.

show abstract

“…The IR spectrum showed absorption bands of hydroxyl (3455 cm −1 ), ester carbonyl (1742 cm −1 ), and amide carbonyl (1657 cm −1 ) functionalities. Analysis of the 1 H and 13 C NMR spectroscopic data (▶ Table 1) as well as 2D NMR (HMQC, HMBC, and NOESY) revealed that the structure of 1 was similar to the pyrrolobenzoxazine sesquiterpenoid CJ-12662 (4) [28,39]. The difference between these two compounds was that the amino group of the pyrrolidine ring in ▶ Table 1 1 H and 13 C NMR spectroscopic data of compounds 1-3 (CDCl 3 , δ in ppm).…”

Section: Resultsmentioning

confidence: 99%

New Pyrrolobenzoxazine Sesquiterpenoid Derivatives from the Fungus Talaromyces trachyspermus

et al. 2021

View full text Add to dashboard Cite

Three new pyrrolobenzoxazine sesquiterpenoids, talatrachyoxazines A – C (1 – 3), together with fourteen known compounds (4 – 17), were isolated from the fungus Talaromyces trachyspermus EU23. Their structures were identified by spectroscopic evidence and mass spectrometry. The absolute configurations of 1 – 3 were determined by NOESY data and comparison of their calculated and experimental electronic circular dichroism (ECD) spectra. Compound 1 showed cytotoxic activity against HelaS3, KB, HT-29, MCF-7, and HepG2 cell lines with IC50 values of 7, 11, 10, 12, and 10 µM, respectively. Compounds 1 and 14 showed weak antibacterial activity against the gram-positive bacteria Bacillus cereus and Bacillus subtilis, while 1 – 3 and 14 showed weak antibacterial activity against the gram-negative bacterium Pseudomonas aeruginosa. In addition, compound 1 showed weak antibacterial activity against Escherichia coli.

show abstract

Full Stereochemical Assignment and Synthesis of the Potent Anthelmintic Pyrrolobenzoxazine Natural Product CJ-12662

Cited by 48 publications

References 7 publications

Five New Cytotoxic Metabolites from the Marine Fungus Neosartorya pseudofischeri

Five New Cytotoxic Metabolites from the Marine Fungus Neosartorya pseudofischeri

Applications of Bartoli indole synthesis

New Pyrrolobenzoxazine Sesquiterpenoid Derivatives from the Fungus Talaromyces trachyspermus

Contact Info

Product

Resources

About