2-Benzoylamino-2-deoxy-2-hydroxymethyl-D-hexono-1,4-lactones: synthesis from D-fructose and utilization in the total synthesis of thermozymocidin (myriocin)

Banfi, Luca; Beretta, M. G.; Colombo, Lino; Gennari, Cesare; Scolastico, Carlo

doi:10.1039/p19830001613

Cited by 40 publications

(6 citation statements)

References 15 publications

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“…It was particularly worth mentioning that Alonso and coworkers 26 starting from D-glucurono-g-lactone 18 have fulfilled a short synthesis of (+)-myriocin 21 employing the key photoinduced addition of MeOH to a chiral ketoxime ether 19 constructing the chiral azo-quaternary center of 20 (Scheme 5). 28,29 Similarly, Tomioka and coworkers 30 have also developed an approach for preparing the enantiomerically enriched sulfonamide through addition of formic acetal to the chiral N-toluenesulfinyl aldimine under promotion of Me 2 Zn/BEt 3 /air.…”

Section: Radical-mediated Addition Of Alcohol and Ether With Alkene A...mentioning

confidence: 99%

Direct Sp3α-C–H activation and functionalization of alcohol and ether

2011

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Seven kinds of sp(3)α-C-H activation/C-C formation reactions of alcohols and ethers have been reviewed in this tutorial review, from the viewpoint of both methodology and synthetic application, towards the efficiency, chemo-, regio- and stereoselectivity, catalytic system, substrate scope and mechanistic study. Section 2 describes radical-mediated α-C-H activation and addition/elimination of ethers with unsaturated (C=C and C[triple bond]C) species. Sections 3-8 discuss the α-C-H activation and additions of alcohols and/or ethers with unsaturated (C=C, C[triple bond]C, C=O and C=N) compounds, which involve the key processes of radical mediation, carbenoid insertion, 1,5-H-migration, oxidative dehydrogenation coupling, transfer hydrogenative coupling, and metal-mediated C=C insertion into the C-H bond.

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Section: Radical-mediated Addition Of Alcohol and Ether With Alkene A...mentioning

confidence: 99%

Direct Sp3α-C–H activation and functionalization of alcohol and ether

2011

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“…However, soon it appeared that myriocin and thermozymocidin are chemically identical (BERDY et al 1981), which was definitely confirmed by PAYETTE and JUST (1981), who also determined its absolute configuration. The antibiotic, identical with natural product, was prepared also by a total synthesis using D-fructose as a source of chirality for the asymetric centres (BANFI et al 1982(BANFI et al , 1983. Since the first producer has not been taxonomically identified, a possible identity of the two producing fungal organisms cannot be excluded.…”

Section: Discussionmentioning

confidence: 99%

Production of thermozymocidin (myriocin) by the pyrenomycete Melanconis flavovirens

Šašek

Sailer

Vokoun

et al. 1989

J. Basic Microbiol.

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Submerged culture of the pyrenomycete Melanconis flavovirens produces a strongly active antifungal antibiotic. The antibiotic was isolated from the culture mash. In purified compound the physico-chemical characteristics, including 1H NMR spectrum, were estimated. The antibiotic was found to be identical with thermozymocidin (myriocin) as confirmed by comparison with synthetically prepared thermozymocidin.

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“…This was supported by mass spectra in which many significant fragmentations were similar (m/z 256, 237, 219, 113, 104 and 102). The advantage of this similarity was taken because the structure and configuration of myriocin has already been exactly characterized (ARAGOZZINI et al 1972, BAGLI et al 1973, JUST and PAYETTE 1980, PAYETTE and JUST 1981, BANFI et al 1982, 1983.…”

Section: Methodsmentioning

confidence: 99%

Flavovirin — a new antifungal antibiotic produced by the pyrenomycete Melanconis flavovirens

Sailer

Šašek

Sejbal

et al. 1989

J. Basic Microbiol.

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The pyrenomycete Melanconis flavovirens was found to produce a mixture of two antifungal antibiotics. The first has been already described; the antibiotic is identical with thermozymocidin (myriocin). The second antibiotic is a new compound, whose isolation and identification is presented in this paper. The chemical structure of this substance (C21H37NO5) was determined to be 2-amino-2-hydroxymethyl-3,4-trans-epoxy-14-oxo-eicos-trans-6-enoic acid. After the producer it was named flavovirin and it possesses strong activity against yeasts and a moderate effectivity against filamentous fungi.

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2-Benzoylamino-2-deoxy-2-hydroxymethyl-D-hexono-1,4-lactones: synthesis from D-fructose and utilization in the total synthesis of thermozymocidin (myriocin)

Cited by 40 publications

References 15 publications

Direct Sp3α-C–H activation and functionalization of alcohol and ether

Direct Sp3α-C–H activation and functionalization of alcohol and ether

Production of thermozymocidin (myriocin) by the pyrenomycete Melanconis flavovirens

Flavovirin — a new antifungal antibiotic produced by the pyrenomycete Melanconis flavovirens

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