Total synthesis of the ionophore antibiotic CP-61,405 (routiennocin)

Díez-Martín, David; Kotecha, Nikesh R.; Ley, Steven V.; Mantegani, Sergio; Menéndez, J. Carlos; Organ, Helen M.; White, Andrew D.; Banks, B. J.

doi:10.1016/s0040-4020(01)80467-1

Cited by 103 publications

(41 citation statements)

References 46 publications

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“…Benzoxazoles are a class of heterocyclic compounds exhibiting therapeutical activities (Figure 2), such as, antifungal agents [38][39][40], cytotoxic compounds [41], as anti-inflammatory agents [42], as HIV-1 protease inhibitor [43], as an antibiotic [44], as CpIMPDH inhibitors [45], nonnucleoside HIV-1 reverse transcriptase inhibitors (NNRTI) [46], and antitumour agents [47].…”

Section: Benzoxazole Amides From Benzoylthioureasmentioning

confidence: 99%

Mechanistic Study on the Formation of Compounds from Thioureas

Laitonjam¹,

Nahakpam²

2018

Density Functional Calculations - Recent Progresses of Theory and Application

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Formation of 2-(N-arylamino)benzothiazole takes place, when N,N 0 -diphenylthioureas are treated with polymer-supported tribromide or with iodine-alumina as catalyst under solvent free conditions. However, when N-substituted-N 0 -benzoylthioureas are treated with polymer-supported tribromide or with iodine-alumina as catalyst either under various conditions or under solvent free conditions, decomposition takes place to give the respective benzamides and thiobenzamides. Mechanistic study of the formation of these compounds is studied using DFT calculations. It is found that electron donating group at the para-position of the aryl group of benzoylthiourea favors the formation of benzamide whereas the presence of electron withdrawing group at para-position of the aryl group of benzoylthiourea, formation of thiobenzamide takes place. When the catalyst is changed to diacetoxyiodobenzene (DIB) under similar reaction conditions, benzoxazole amides are formed; expected benzothiazoles or the decomposition products are not obtained. Mechanistic study of the reaction using DFT calculation again shows that the reaction followed through carbodiimide intermediate undergoes the formation of C-O bond in benzoxazole moiety, instead of the expected C-S bond formation of benzothiazole moiety via a sequential acylation and deacylation process.

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Section: Benzoxazole Amides From Benzoylthioureasmentioning

confidence: 99%

Mechanistic Study on the Formation of Compounds from Thioureas

Laitonjam¹,

Nahakpam²

2018

Density Functional Calculations - Recent Progresses of Theory and Application

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“…The reagent TPAP/NMO/PMS/CH 2 Cl 2 was also used in a step in the synthesis of the colony-stimulating factor leustroducsin B (TPAP) [96]; for the antiparasitic spiroketal macrolide (+)-milbemycin a 1 [97]; the antiparasitic insecticide (+)-milbemycin-b 1 (secondary alcohol to a ketone step also) [98]; the sesquiterpenes nortrilobolide, thapsivillosin F and trilobolide (a second step involving the reagent was a lactol-to-lactone transformation) [64]; the marine alkaloid norzoanthamine (secondary alcohol to ketone step also) [99]; the eunicellin ophirin B [84]; the biologically active diterpene phomactin A [100]; the macrolide prelactone B (primary alcohol to lactone) [101]; the spiroketal ionophore antibiotic routiennocin [102,103]; the macrolides salicylihalamides A and B [104]; the anti-tumour microtubulin stablising agents sarcodictyins A and B [105]; the polypropionate siphonarienolone [106]; the antibiotic (+)-tetronomycin [107], and the aglycon of the antitumour antibiotic tetronolide [108]. During synthesis of the protein phosphatase inhibitor okadaic acid three oxidations with TPAP/NMO/PMS/CH 2 Cl 2 were used, two of a primary alcohol to aldehydes and one of a diol to a lactone [109]; the reagent was used in the synthesis of a fragment of the antibiotic sorangicin A [110].…”

Section: Natural Product/pharmaceutical Syntheses Involving Primary Amentioning

confidence: 99%

Oxidation of Alcohols, Carbohydrates and Diols

Griffith

2009

Catalysis by Metal Complexes

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This is one of the most important classes of oxidation effected by Ru complexes, particularly by RuO 4 , [RuO 4 ] − , [RuO 4 ] 2− and RuCl 2 (PPh 3 ) 3 , though in fact most Ru oxidants effect these transformations. The chapter covers oxidation of primary alcohols to aldehydes (section 2.1), and to carboxylic acids (2.2), and of secondary alcohols to ketones (2.3). Oxidation of primary and secondary alcohol functionalities in carbohydrates (sugars) is dealt with in section 2.4, then oxidation of diols and polyols to lactones and acids (2.5). Finally there is a short section on miscellaneous alcohol oxidations in section 2.6.In this chapter the first of the two most important categories of oxidations catalysed by Ru complexes (the other being alkene and alkyne oxidations in Chapter 3) are considered. The approach in this and subsequent chapters differs from that of Chapter 1, concentrating here on the substrate rather than on the oxidant. The text is divided into the categories of alcohols and their oxidations. There are summaries in section 2.3.6 of systems of limited applicability which are mentioned only in Chapter 1, and in section 2.3.7 of large-scale (>1 g) oxidations.The first oxidations of alcohols by stoicheiometric RuO 4 /H 2 O were reported in 1958, of primary alcohols to aldehydes or carboxylic acids and secondary alcohols to ketones [1]. The first Ru-catalysed oxidation of an alcohol was reported in 1965 when Parikh and Jones used RuO 2 /aq. Na(IO 4 )/CCl 4 1 ( Table 2.3) [2] to oxidise secondary alcohol groups in carbohydrates.Oxidation of alcohols is the most frequently reviewed topic for Ru-catalysed oxidations [3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20]. Mechanisms of alcohol oxidation by Ru complexes have been reviewed [21].

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“…a range of benzoxazole derivatives were extensively considered for their biological and pharmacological activities concerning antibiotic [1,2] antimicrobial [3][4][5] antifungal [6][7][8] and antitumor activities [9][10][11]. In addition, benzoxazole analogous and their metallic complexes have been widely applied for use in chemistry and medicine with various transition metal ions via nitrogen donor atoms [12][13][14].…”

Section: Introductionmentioning

confidence: 99%