Intramolecular radical cyclization of phenolic enolates

Kende, Andrew S.; Koch, Kevin; Smith, C.

doi:10.1021/ja00215a034

Cited by 57 publications

(19 citation statements)

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“…As compound 29 was selectively generated in our system, the formation of such a spirocyclic frame would be more preferable under Brønsted acid-mediated Friedel-Crafts cyclization, although Kende and co-worker reported an example of ring expansion in a spirocyclic frame via dienone-phenol rearrangements in several spirocyclic dienone derivatives in the presence of CF 3 CO 2 H in CH 2 Cl 2 . 37 Successful ring expansion was observed by using Lewis acid for dienone-phenol rearrangements with our substrate. We found that the spirocyclic frame is formed in the presence of a Brønsted acid, such as H 2 SO 4 and AcOH, but not in the presence of Lewis acids.…”

Section: Resultsmentioning

confidence: 91%

Total synthesis of (±)-naphthacemycin A9, possessing both antibacterial activity against methicillin-resistant Staphylococcus aureus and circumventing effect of β-lactam resistance

et al. 2016

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The total synthesis of KB-3346-5A 9 , named naphthacemycin A 9 , has been accomplished by combining the Dötz reaction and Suzuki-Miyaura cross coupling as well as employing Friedel-Crafts reaction with dienone-phenol rearrangement as key steps. We also describe the preparation of the simplified tetarimycin A and naphthacemycin A analogs as a model study, which coincidentally reveal unique properties of naturally occurring naphthacene-5,6,11(12H)-trione framework. The synthesized compounds were evaluated for antibacterial activity against methicillin-resistant Staphylococcus aureus and vancomycin-resistant Enterococcus (VRE) to elucidate their structure-activity relationships (SARs), the results of which agreed with a previously reported preliminary SAR study of tetarimycin A.

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Section: Resultsmentioning

confidence: 91%

Total synthesis of (±)-naphthacemycin A9, possessing both antibacterial activity against methicillin-resistant Staphylococcus aureus and circumventing effect of β-lactam resistance

et al. 2016

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“…170–172 Treatment of phenolic nitroalkane 38-1 with K 3 Fe(CN) 6 in dilute KOH solution provided spirocyclicdienone 38-2 through a stepwise single electron transfer process. Formation of cyclopropane intermediate 38-3 followed by ring expansion of 38-4 afforded tropone 38-5 in good yield.…”

Section: Synthesis Of Naturally Occurring Tropones and Tropolonesmentioning

confidence: 99%

Synthesis of naturally occurring tropones and tropolones

et al. 2014

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Tropones and tropolones are an important class of seven-membered non-benzenoid aromatic compounds. They can be prepared directly by oxidation of seven-membered rings. They can also be derived from cyclization or cycloaddition of appropriate precursors followed by elimination or rearrangement. This review discusses the types of naturally occurring tropones and tropolones and outlines important methods developed for the synthesis of tropone and tropolone natural products.

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“…The ethereal solution was dried over Na 2 SO 4 and concentrated in a vacuum. The resulting oil was chromatographed on silica gel.…”

Section: Reaction Of 1-hexene (1) and 2-butanone With Cs In Methanol-mentioning

confidence: 99%

Reaction of olefins using cerium(IV) sulfate tetrahydrate in carbonyl compounds-H2O

Itoh

Ueki

Mikami

et al. 2005

Appl. Organometal. Chem.

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The reaction of olefins with cerium(IV) sulfate tetrahydrate [Ce(SO 4 ) 2 ·4H 2 O, CS] in acetone-H 2 O under reflux for 5 h gave 2-oxo-and 2-oxo-5-hydroxy derivatives. In this reaction, the yields of 2-oxo-5-hydroxy derivatives were dependent on the quantity of H 2 O. Moreover, the reaction of α, β-unsaturated ketones with CS in acetone-H 2 O yielded 2,7-dioxo-3-hydroxy or 3,8-dioxo-4-hydroxy derivatives. The reaction mechanism is also discussed.

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Intramolecular radical cyclization of phenolic enolates

Cited by 57 publications

References 0 publications

Total synthesis of (±)-naphthacemycin A9, possessing both antibacterial activity against methicillin-resistant Staphylococcus aureus and circumventing effect of β-lactam resistance

Total synthesis of (±)-naphthacemycin A9, possessing both antibacterial activity against methicillin-resistant Staphylococcus aureus and circumventing effect of β-lactam resistance

Synthesis of naturally occurring tropones and tropolones

Reaction of olefins using cerium(IV) sulfate tetrahydrate in carbonyl compounds-H2O

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