Photolactonisierung: Ein neuer synthetischer Zugang zu Makroliden

Quinkert, Gerhard; Billhardt, Uta‐Maria; Jakob, H.; Fischer, Gerd; Glenneberg, Jürgen; Nagler, Peter; Autze, Volker; Heim, Nana; Wacker, Manfred; Schwalbe, Thomas; Kurth, Yvonne; Bats, Jan W.; Dürner, Gerd; Zimmermann, Gottfried; Kessler, Horst

doi:10.1002/hlca.19870700326

Cited by 42 publications

(12 citation statements)

References 73 publications

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“…The work-up was performed by the same method as described above. All products except for 13 [6] and 24 [7] were commercially available, and were identified through comparison of the isolated product with an authentic sample. asc.wiley-vch.de…”

Section: Procedures For the Oxidation Of Various Substrates To Aldehydmentioning

confidence: 99%

Preparation of Hydroperoxides byN-Hydroxyphthalimide-Catalyzed Aerobic Oxidation of Alkylbenzenes and Hydroaromatic Compounds and Its Application

2001

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An efficient approach to phenols and aldehydes through the formation of hydroperoxides from alkylbenzenes was successfully achieved by aerobic oxidation using N‐hydroxyphthalimide (NHPI) as a catalyst. The oxidation of various alkylbenzenes with dioxygen by NHPI followed by treatment with a Lewis acid or triphenylphosphine led to phenols or aldehydes, respectively, in good yields. For example, the aerobic oxidation of cumene in the presence of a catalytic amount of NHPI at 75 °C and subsequent treatment with H2SO4 gave phenol in 77% yield. 1,4‐Dihydroxybenzene (61%) and 4‐isopropylphenol (33%) were obtained from 1,4‐diisopropylbenzene. On the other hand, dibenzyl ether was converted into phenol or benzaldehyde upon treatment of the resulting hydroperoxide with InCl3 or PPh3, respectively.

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Section: Procedures For the Oxidation Of Various Substrates To Aldehydmentioning

confidence: 99%

Preparation of Hydroperoxides byN-Hydroxyphthalimide-Catalyzed Aerobic Oxidation of Alkylbenzenes and Hydroaromatic Compounds and Its Application

2001

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“…Die sogenannte Photolactonisierung [13] fand in der Mitte der Synthese statt. Das erste stereogene Zentrum (an C( 17)) war vorher rnit Hilfe eines chiralen, nicht-racemischen Synthesebausteins aus nachwachsenden Rohstoffen ((-)-(S)-Methyloxiran (C) aus (-)-(S)-Milchsaureethylester), die ubrigen stereogenen Zentren (an C(4), C(5) und C(6)) waren nachher in diastereoselektiven Syntheseschritten eingefuhrt worden.…”

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Weitere Beiträge zur Synthese von (+)‐Aspicilin

Quinkert¹,

Döller²,

Eichhorn³

et al. 1990

Helvetica Chimica Acta

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Albert Eschenmoser zum 65. Geburtstag gewidmet (2.VI11.90) Further Contributions to the Synthesis of (+)-AspicilinThere are two reasons to try to find out, whether the initial and final parts of the 'photochemical synthesis' of the ]&membered lichen macrolide (+)-aspicilin (5a) can be improved (cf: Schemes I and 2). This synthesis acts as an indicator for the utility of the earlier introduced photolactonization and as a source of large-ring-sized lactones, objects for computer-assisted conformational analysis.

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“…134, Figure 33), as first observed by Hart and co-workers [160][161][162]. Early on, ortho-quinol acetates were used as substrates to study the photochemical behavior of cyclohexa-2,4-dienones [158,159], and numerous examples have been described by Quinkert and co-workers [160,163,164]. In contrast to the photolytic ring-opening of cyclohexa-2,4-dienones bearing two carbon substituents at their 6-position, ortho-quinol acetates of type 123 only led to diene ketenes with the (5E )-configuration ( Figure 31).…”

Section: Photochemical Rearrangementsmentioning

confidence: 84%

Oxidative Conversion of Arenols into ortho ‐Quinols and ortho ‐Quinone Monoketals – A Useful Tactic in Organic Synthesis

Quideau

2002

Modern Arene Chemistry

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The oxidative activation of arenes is a powerful and versatile synthetic tactic that enables dearomatization to give useful synthons. Central to this chemistry are hydroxylated arenes or arenols, the phenolic functions of which can be exploited to facilitate the dearomatizing process by two-electron oxidation. Suitably substituted arenols can hence be converted, with the help of oxygen-or carbon-based nucleophiles, into ortho-quinone monoketals and ortho-quinols. These 6-oxocyclohexa-2,4-dienones are ideally functionalized for the construction of many complex and polyoxygenated natural product architectures. Today, the inherent and multiple reactivity of arenol-derived ortho-quinone monoketals and orthoquinols species is finding numerous and, in many cases, biomimetic applications in modern organic synthesis. 15.1

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Photolactonisierung: Ein neuer synthetischer Zugang zu Makroliden

Cited by 42 publications

References 73 publications

Preparation of Hydroperoxides byN-Hydroxyphthalimide-Catalyzed Aerobic Oxidation of Alkylbenzenes and Hydroaromatic Compounds and Its Application

Preparation of Hydroperoxides byN-Hydroxyphthalimide-Catalyzed Aerobic Oxidation of Alkylbenzenes and Hydroaromatic Compounds and Its Application

Weitere Beiträge zur Synthese von (+)‐Aspicilin

Oxidative Conversion of Arenols into ortho ‐Quinols and ortho ‐Quinone Monoketals – A Useful Tactic in Organic Synthesis

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