Total Synthesis of (±)‐γ‐Rubromycin on the Basis of Two Aromatic Pummerer‐Type Reactions

Akai, Shuji; Kakiguchi, Keisuke; Nakamura, Yuka; Kuriwaki, Ikumi; Dohi, Toshifumi; Harada, Shusaku; Kubo, Ozora; Morita, Nobuyoshi; Kita, Yasuyuki

doi:10.1002/anie.200702382

Cited by 78 publications

(70 citation statements)

References 43 publications

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“…For example, Kita et al used a double Pummerer-like rearrangement in the first total synthesis of γ-rubromycin [196], while acid-catalyzed [153,[197][198][199][200] and oxidative rearrangements [201], have also been reported. These methods can, however, be highly substrate dependent.…”

Section: Rearrangementsmentioning

confidence: 97%

Synthesis of 5,6- and 6,6-Spirocyclic Compounds

Brimble

Stubbing

2013

Synthesis of Saturated Oxygenated Heterocycles I

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Section: Rearrangementsmentioning

confidence: 97%

Synthesis of 5,6- and 6,6-Spirocyclic Compounds

Brimble

Stubbing

2013

Synthesis of Saturated Oxygenated Heterocycles I

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“…However a-rubromycin has an IC 50 value of &200 lM (Ueno et al 2000). Due to the interesting potentiality of c-rubromycin, a research group has successfully designed the total chemical synthesis of cRubromycin in 2007 (Akai et al 2007). …”

Section: Compounds Directly Interacting With Functional Catalytic Submentioning

confidence: 98%

Human telomerase inhibitors from microbial source

Kiran

Palaniswamy

Angayarkanni

2015

World J Microbiol Biotechnol

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Telomerase enzyme inhibitors have gained attention of scientific field due to the specificity of action of telomerase based therapies. Some telomerase have good combinatorial action with certain DNA damaging drugs. Natural compounds isolated from microbes provide a new scope of screening and large scale production of telomerase inhibitors. This review emphasizes the biochemistry and mode of action of different types of telomerase inhibitors isolated from microbial sources. Also elaborates on classification of telomerase inhibitors based on their mode of action in cancer cells.

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“…However, despite these substantial efforts, only two successful total syntheses of the rubromycin family had been achieved when we started our investigations in this area. Danishefsky and co-workers completed their synthesis of heliquinomycin (19) in 2001 [19], which was followed six years later by the total synthesis of γ-rubromycin (17) by Kita et al [20].…”

Section: Rubromycinmentioning

confidence: 99%

Synthetic approaches to [5,6]-benzannulated spiroketal natural products

McLeod

Brimble

Rathwell

et al. 2011

Pure and Applied Chemistry

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Studies toward the synthesis of three biologically active [5,6]-benzannulated spiroketal natural products are described. The first total synthesis of paecilospirone is reported, employing a late-stage, pH-neutral spiroketalization. A formal synthesis of γ-rubromycin is described, where the spiroketal moiety is formed by delicate manipulation of the electronic properties of the spirocyclization precursor. Finally, model work toward the total synthesis of berkelic acid is summarized, introducing a novel Horner-Wadsworth-Emmons/oxa-Michael (HWE/oxa-M) cascade to access the spiroketal precursor.Sonogashira reaction of 25 and 26 afforded propargylic alchohol 24 (Scheme 8). We found that the use of a non-amine base (cesium carbonate) and degassed solvents were required to minimize the formation of homocoupled product. Reduction of the triple bond by hydrogenation over 10 % Pd/C buffered with sodium bicarbonate, followed by oxidation of the secondary alcohol with o-iodosoxybenzoic acid (IBX) provided ketone 23. The key spiroketalization step was then attempted using the mild procedure previously developed by our group [23]. Pleasingly, treatment of 23 with silica-supported sodium hydrogen sulfate in dichloromethane afforded spiroketal 35 in 80 % yield. Finally, selective saponification of the aliphatic ester and adjustment of the naphthalene moiety oxidation state M. C. MCLEOD et al. Scheme 7 Synthesis of iodide 26. Scheme 8 Completion of formal synthesis. Brought to you by | Scheme 11 Synthesis of bromide 38 and completion of total synthesis. Brought to you by |

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Total Synthesis of (±)‐γ‐Rubromycin on the Basis of Two Aromatic Pummerer‐Type Reactions

Cited by 78 publications

References 43 publications

Synthesis of 5,6- and 6,6-Spirocyclic Compounds

Synthesis of 5,6- and 6,6-Spirocyclic Compounds

Human telomerase inhibitors from microbial source

Synthetic approaches to [5,6]-benzannulated spiroketal natural products

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