Synthesis of Medium‐Ring and Iodinated Biaryl Compounds by Organocuprate Oxidation

Surry, D.; Su, Xueying; Fox, David J.; Franckevičius, Vilius; Macdonald, Simon J. F.; Spring, David R.

doi:10.1002/anie.200462642

Cited by 64 publications

(28 citation statements)

References 47 publications

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“…Su et al employed an organocuprate oxidative intramolecular biaryl-bond forming reaction to a halogenated benzoyl derivative (9). Treatment of 9 with isopropylmagnesium bromide, followed by transmetalation with CuBrSMe 2 and subsequent cuprate oxidation afforded 10 [30]. The reaction proceeded with complete diastereoselectivity without any dimeric side products.…”

Section: Chemical Synthesis Of Ellagitannins By Biaryl Coupling Of Gamentioning

confidence: 99%

Biomimetic Synthesis and Related Reactions of Ellagitannins

Tanaka

Kouno

Nonaka³

2011

Biomimetic Organic Synthesis

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Section: Chemical Synthesis Of Ellagitannins By Biaryl Coupling Of Gamentioning

confidence: 99%

Biomimetic Synthesis and Related Reactions of Ellagitannins

Tanaka

Kouno

Nonaka³

2011

Biomimetic Organic Synthesis

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“…Based on a double organocuprate oxidation strategy, Spring and coworkers reported the total synthesis of (±)-deoxyschizandrin in 2012 (Scheme 10) [67]. Symmetrical 1,3-diene 58 was prepared by the homo-coupling of alkenyl iodide 57 through a mild metalation, magnesio-cuprate transmetalation and subsequent oxidation using 61 as the oxidant [68]. Subsequent hydrogenation afforded 59 as a mixture of two diastereoisomers.…”

Section: Advances In Synthesis Of Dibenzocyclooctadiene Serivativesmentioning

confidence: 99%

Advances in the Synthesis of Lignan Natural Products

Fang

2018

Molecules

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Lignans comprise a family of secondary metabolites existing widely in plants and also in human food sources. As important components, these compounds play remarkable roles in plants’ ecological functions as protection against herbivores and microorganisms. Meanwhile, foods rich in lignans have revealed potential to decrease of risk of cancers. To date, a number of promising bioactivities have been found for lignan natural products and their unnatural analogues, including antibacterial, antiviral, antitumor, antiplatelet, phosphodiesterase inhibition, 5-lipoxygenase inhibition, HIV reverse transcription inhibition, cytotoxic activities, antioxidant activities, immunosuppressive activities and antiasthmatic activities. Therefore, the synthesis of this family and also their analogues have attracted widespread interest from the synthetic organic chemistry community. Herein, we outline advances in the synthesis of lignan natural products in the last decade.

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“…[6] Inspired by the pioneering work of Yamamoto and Marouka, [7] Ricci and co-workers, [8] Lipshutz et al, [9] and others, [10] who described the oxidative coupling of amidocuprates or organo(cyano)cuprates using oxygen or 1,3dinitrobenzene derivatives as oxidants, we have now examined the oxidative amination reaction of various polyfunctional amidocuprates and developed an experimental procedure that allows the preparation of primary, secondary, as well as tertiary aromatic and heterocyclic amines.…”

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confidence: 99%