Facile synthesis of caerulomycin E by the formation of 2,2′-bipyridine core via a 2-pyridyl substituted 4H-pyran-4-one. Formal synthesis of caerulomycin A

Bobrov, D. N.; Tyvorskii, V. I.

doi:10.1016/j.tet.2010.05.024

Cited by 14 publications

(8 citation statements)

References 17 publications

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“…A series of other important heterocyclic aldehydes and ketones were synthesized by microwave- assisted selenium(IV) oxide oxidation [65,66]. The crucial step in synthesis of the antibiotic caerulomycin E was selenium(IV) oxide oxidation of a methyl group to a formyl group in 4-methoxy-6-methyl-2,2′-bipyridine [67]. On the way to synthesize verdamycin C2, the corresponding aldehydes were obtained by oxidation of allylic primary azides of 2-substituted dihydro[2 H ]pyrans with SeO 2 [68].…”

Section: Selenium(iv) Oxide and Selenic(iv) Acid As Oxidizing Agenmentioning

confidence: 99%

Developments in Synthetic Application of Selenium(IV) Oxide and Organoselenium Compounds as Oxygen Donors and Oxygen-Transfer Agents

2015

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A variety of selenium compounds were proven to be useful reagents and catalysts for organic synthesis over the past several decades. The most interesting aspect, which emerged in recent years, concerns application of hydroperoxide/selenium(IV) oxide and hydroperoxide/organoselenium catalyst systems, as "green reagents" for the oxidation of different organic functional groups. The topic of oxidations catalyzed by organoselenium derivatives has rapidly expanded in the last fifteen years This paper is devoted to the synthetic applications of the oxidation reactions mediated by selenium compounds such as selenium(IV) oxide, areneseleninic acids, their anhydrides, selenides, diselenides, benzisoselenazol-3(2H)-ones and other less often used other organoselenium compounds. All these compounds have been successfully applied for various oxidations useful in practical organic syntheses such as epoxidation, 1,2-dihydroxylation, and α-oxyfunctionalization of alkenes, as well as for ring contraction of cycloalkanones, conversion of halomethyl, hydroxymethyl or active methylene groups into formyl groups, oxidation of carbonyl compounds into carboxylic acids and/or lactones, sulfides into sulfoxides, and secondary amines into nitrones and regeneration of parent carbonyl compounds from their azomethine derivatives. Other reactions such as dehydrogenation and aromatization, active carbon-carbon bond cleavage, oxidative amidation, bromolactonization and oxidation of bromide for subsequent reactions with alkenes are also successfully mediated by selenium (IV) oxide or organoselenium compounds. The oxidation mechanisms of ionic or free radical character depending on the substrate and oxidant are discussed. Coverage of the literature up to early OPEN ACCESSMolecules 2015, 20 10206 2015 is provided. Links have been made to reviews that summarize earlier literature and to the methods of preparation of organoselenium reagents and catalysts.

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Section: Selenium(iv) Oxide and Selenic(iv) Acid As Oxidizing Agenmentioning

confidence: 99%

Developments in Synthetic Application of Selenium(IV) Oxide and Organoselenium Compounds as Oxygen Donors and Oxygen-Transfer Agents

2015

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“…Caerulomycins, a family of alkaloids featuring a 2,2′-bipyridine skeleton, were first discovered from Streptomyces caeruleus . Their interesting activities, such as antibiotic, , phytotoxic and immunosuppressant activities, and their unique structure have attracted great attention of chemists and biologists . Recently, we reported a number of new caerulomycin analogues, such as caerulomycins F–K and cyanogrisides A–D, from the marine-derived actinomycete strain Actinoalloteichus cyanogriseus WH1-2216-6.…”

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Acyclic Congeners from Actinoalloteichus cyanogriseus Provide Insights into Cyclic Bipyridine Glycoside Formation

Zhu

Mei

et al. 2014

Org. Lett.

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Inactivation of the O-methyltransferase gene crmM of Actinoalloteichus cyanogriseus WH1-2216-6 led to a mutant that produced three new acyclic bipyridine glycosides, cyanogrisides E-G (1-3). Further chemical analysis of the wild strain yielded 1 and another new analogue, cyanogriside H (4). Compounds 1-4 possess a skeleton consisting of a 2,2'-bipyridine and a d-quinovose or l-rhamnose sugar moiety. Cyanogriside G (3) was considered to be a key biosynthetic intermediate of the cyclic bipyridine glycosides cyanogrisides A-D. Compounds 2 and 3 showed cytotoxicities against HCT116 and HL-60 cells, and compounds 1 and 4 were cytotoxic on K562 cells.

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“…Caerulomycins were found to have strong antifungal, antiamoebic, and antitumor activities, and mild antibacterial activities. , Caerulomycin A ( 1 ) was also demonstrated to have novel bioactivity with remarkable promise in immunosuppression . The unique structure of caerulomycins and their significant bioactivities attracted many synthetic efforts, with accomplishments of the total synthesis of caerulomycins A-C and E . The biosynthetic studies of 1 were limited to earlier feeding experiments with labeled putative precursors, revealing the origin of the first pyridine ring from lysine via picolinic acid as an intermediate .…”

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Identification of Caerulomycin A Gene Cluster Implicates a Tailoring Amidohydrolase

Zhu

Lin

et al. 2012

Org. Lett.

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The biosynthetic gene cluster for caerulomycin A (1) was cloned and characterized from the marine actinomycete Actinoalloteichus cyanogriseus WH1-2216-6, which revealed an unusual hybrid polyketide synthase (PKS)/nonribosomal peptide synthetase (NRPS) system. The crmL disruption mutant accumulated caerulomycin L (2) with an extended L-leucine at C-7, implicating an amidohydrolase activity for CrmL. The leucine-removing activity was confirmed for crude CrmL enzymes. Heterologous expression of the 1 gene cluster led to 1 production in Streptomyces coelicolor.

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Facile synthesis of caerulomycin E by the formation of 2,2′-bipyridine core via a 2-pyridyl substituted 4H-pyran-4-one. Formal synthesis of caerulomycin A

Cited by 14 publications

References 17 publications

Developments in Synthetic Application of Selenium(IV) Oxide and Organoselenium Compounds as Oxygen Donors and Oxygen-Transfer Agents

Developments in Synthetic Application of Selenium(IV) Oxide and Organoselenium Compounds as Oxygen Donors and Oxygen-Transfer Agents

Acyclic Congeners from Actinoalloteichus cyanogriseus Provide Insights into Cyclic Bipyridine Glycoside Formation

Identification of Caerulomycin A Gene Cluster Implicates a Tailoring Amidohydrolase

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