Regiospecific synthesis of bromojuglone derivatives

Heinzman, Stephen W.; Grunwell, John R.

doi:10.1016/s0040-4039(00)77843-9

Cited by 50 publications

(21 citation statements)

References 7 publications

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“…There is insufficient data concerning quinones and cancer. The higher quinones are less of a problem because of their decreased volatility (222)(223)(224)(225) CITED PUBLICATIONS…”

Section: Health and Safety Factorsmentioning

confidence: 99%

Quinones

Finley

2016

Kirk-Othmer Encyclopedia of Chemical Technology

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Quinones, possessing two α,β‐unsaturated carbonyl groups usually in a six‐carbon atom ring, represent a unique structural unit. Their centrality in the synthesis of such important commercial substances as dyes and pharmaceuticals has resulted in extensive studies. In living matter, they are ubiquitous and vital to human metabolism. Quinones are of special interest to biochemists and to both synthetic and theoretical organic chemists. The types of reactions most often reported are nucleophilic addition, photochemistry, cycloaddition, electrophilic addition, radical alkylation, electrochemical, oxidation, and nucleophilic substitution. The synthesis of quinones is usually accomplished through oxidation of phenols or anilines.

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“…There is insufficient data concerning quinones and cancer. The higher quinones are less of a problem because of their decreased volatility (222)(223)(224)(225) CITED PUBLICATIONS…”

Section: Health and Safety Factorsmentioning

confidence: 99%

Quinones

Finley

2016

Kirk-Othmer Encyclopedia of Chemical Technology

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“…Compounds that have triazoles, chalcone and quinone nuclei, separately or together with other nuclei, have important pharmacological properties such as antibacterial, antifungal, antiprotozoal, antiviral, antiallergic, anticancer, antiinflammatory, among others [1][2][3][4][5][6] . In this work, we propose the synthesis of molecules bearing in their structures these 3 important nuclei ( Figure 1 …”

Section: Introductionmentioning

confidence: 99%

Synthesis of naphthoquinone derivatives with potential pharmacological activity

Oliveira¹,

Andrade²

2013

Proceedings of the 14th Brazilian Meeting on Organic Synthesis Proceedings

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“…Therefore, we next tried an alternative preparation of naphthalenepropanoic acid 13 from 14 by stepwise introduction of the propanoic acid unit as shown in Scheme 4. Diacetate 23, obtained by nonselective acetylation of 14, was subjected to oxidative bromination with N-bromosuccinimide (NBS) in aqueous AcOH to smoothly give 2-bromo-5-O-acetyljuglone (24) [20]. After replacement of the acetyl function of 24 by the Me group, reduction of 26 with SnCl 2 followed by methylation under nonaqueous conditions [21] afforded 2-bromo-1,4,5-trimethoxynaphthalene (27).…”

mentioning

confidence: 99%

“…), CH 2 Cl 2 , 08, 1.5 h. d) KF (0.1 equiv. ), DMSO, air, r.t.dioxonaphthalene-2-propanoate(20). A soln.…”

mentioning

confidence: 99%

Synthetic Studies on Kinamycin Antibiotics: Synthesis of a Trioxygenated Benz[f]indenone and its Diels–Alder Reaction to a Kinamycin Skeleton

Kitani

Morita

Kumamoto

et al. 2002

HCA

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A benzo [b]fluorene skeleton such as 10, a basic four-ring system in the revised diazo structures 3 of kinamycin antibiotics, was synthesized by Diels-Alder reaction between dienophile 4,7,8-trioxygenated 1H-benz[f]inden-1-one 11 and Danishefsky-type diene 7. The indenone 11 was prepared by deoxygenation of 2,3-dihydro-1H-benz[f]inden-1-one 12 with the inexpensive 1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide (IBX) after modification of the known protocol. Indenone 12 in turn was obtained from naphthalene-1,5-diol (14) via an intramolecular Friedel-Crafts cyclization of naphthalene-2-propanoic acid 13 as a key step.1. Introduction. ± Kinamycin antibiotics [1], strongly active against gram-positive bacteria, were isolated from Streptomyces murayamaensis [2] and established to be composed of a 6-6-5-6 ring system with a highly oxygenated cyclohexene moiety (D ring) [3]. However, there has been some confusion regarding their structures as mentioned in our previous papers [4]; i.e., benzo[b]carbazolequinone-derived cyanamides 1 and 2 had been first characterized as the basic structures of kinamycins [3] and prekinamycin [5] (a biosynthetic precursor of kinamycins [6]), respectively; however, these structures were revised to diazobenzo[b]fluorenediones 3 and 4 after reexamination of X-ray crystallographic analysis and synthesis of an N-cyanamide structure proposed for prekinamycin [7]. Furthermore, a quite recent investigation [8] indicated that an isomeric benzo[a]fluorene 5 could be a more reasonable structure for prekinamycin than 4 and, accordingly, it was proposed that compounds 4 and 5 should be newly named as isoprekinamycin and prekinamycin, respectively. Thus, synthetic approaches to kinamycin derivatives with the revised diazobenzo[b]fluorene skeleton are necessary for their structural establishment.We had started to synthesize benzo[b]fluorene skeletons before the further revision [8] of the prekinamycin structure and achieved in a model study the stereoselective preparation of the diazofluorene 9 with a 3,4,5,6-tetraoxygenated cyclohexene-ring moiety and the correct relative configuration (cis,trans,trans for the OH groups) of the kinamycin skeleton [4]. In this synthesis, the Diels ± Alder reaction of 4-(benzyloxy)-1H-inden-1-one (6) with Danishefsky-type diene 7 [9] had been used for the ringsystem construction such as that of 8 (Scheme 1).We now report the synthesis of a trioxygenated 1H-benz[f]inden-1-one 11 by dehydrogenation of the corresponding indanone 12, which was independently prepared from naphthalene-1,5-diol (14) by an improved synthetic method. The dehydrogenation of 12 was achieved with 1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide (IBX), and the Diels ± Alder reaction of the resulting 11 with 7 led to the benzo[b]fluorene derivative 10, which contains the basic ring system of the revised structures 3 of the kinamycin antibiotics.

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Regiospecific synthesis of bromojuglone derivatives

Cited by 50 publications

References 7 publications

Quinones

Quinones

Synthesis of naphthoquinone derivatives with potential pharmacological activity

Synthetic Studies on Kinamycin Antibiotics: Synthesis of a Trioxygenated Benz[f]indenone and its Diels–Alder Reaction to a Kinamycin Skeleton

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