Practical synthesis of the rebeccamycin aglycone and related analogs by oxidative cyclization of bisindolylmaleimides with a Wacker-type catalytic system

Wang, Jianji; Rosingana, Miguel; Watson, Daniel; Dowdy, Eric D.; Discordia, Robert P.; Soundarajan, Nachimuthu; Li, Wen-Sen

doi:10.1016/s0040-4039(01)02021-4

Cited by 36 publications

(22 citation statements)

References 15 publications

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“…179 In this case the intramolecular coupling of two indole units was used to prepare the carbazole core (eq 56). In a similar vein, Boger coupled two pyrroles tethered through an amide to generate the C−C linkage between two of the pyrrole units of prodigiosin (eq 57).…”

Section: Applications Of C−h Bond Functionalization To the Synthesis mentioning

confidence: 99%

Evolution of C–H Bond Functionalization from Methane to Methodology

2015

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This Perspective presents the fundamental principles, the elementary reactions, the initial catalytic systems, and the contemporary catalysts that have converted C−H bond functionalization from a curiosity to a reality for synthetic chemists. Many classes of elementary reactions involving transition-metal complexes cleave C−H bonds at typically unreactive positions. These reactions, coupled with a separate or simultaneous functionalization process lead to products containing new C−C, C−N, and C−O bonds. Such reactions were initially studied for the conversion of light alkanes to liquid products, but they have been used (and commercialized in some cases) most often for the synthesis of the more complex structures of natural products, medicinally active compounds, and aromatic materials. Such a change in direction of research in C−H bond functionalization is remarkable because the reactions must occur at an unactivated C−H bond over functional groups that are more reactive than the C−H bond toward classical reagents. The scope of reactions that form C−C bonds or install functionality at an unactivated C−H bond will be presented, and the potential future utility of these reactions will be discussed.

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Section: Applications Of C−h Bond Functionalization To the Synthesis mentioning

confidence: 99%

Evolution of C–H Bond Functionalization from Methane to Methodology

2015

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“…In 2001, Wang et al. from Bristol–Myers Squibb applied the palladium‐catalyzed CH/CH coupling to the synthesis of rebeccamycin aglycone 54 (Scheme ) 49. Although the construction of the indolo[2,3‐ a ]‐pyrrolo[3,4‐ c ]carbazole ring system from bisindolylmaleimide 52 had already been achieved with oxidants such as DDQ, phenyliodinebis(trifluoroacetate) (PIFA), phenyliodinediacetate (PIDA), I 2 , CuCl 2 , and a stoichiometric amount of a palladium complex,50 there had been no reports of catalytic conditions to achieve this transformation in high chemical yield.…”

Section: Cc Bond Formationmentioning

confidence: 99%

CH Bond Functionalization: Emerging Synthetic Tools for Natural Products and Pharmaceuticals

2012

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“…The reaction conditions are based upon those developed by Jeffery for the Heck reaction and permit that the palladium catalyzed reactions occur under milder conditions than those originally reported in similar biaryl coupling reactions . The syntheses were completed through the use of combined reduction (BH 3 .THF and NaCNBH 3 ) and oxidation (KMnO 4 ) reactions or by oxidation of the products obtained from the borane reduction of the respective 37 (Scheme ) [33b] …”

Section: Pd‐catalyzed Intramolecular C–h Arylation (C–h/c–x Coupling)mentioning

confidence: 99%

“…Transition‐metal‐catalyzed direct C–H functionalization has emerged as an attractive strategy for the synthesis of heterocyclic compounds . The ability of transition metals such as Pd, Pt, Ru, Rh, Re, Ir, Ni, Fe and Cu to activate C–H bonds has been used extensively to construct C–C and C–heteroatom bonds in organic synthesis.…”

Section: Introductionmentioning

confidence: 99%