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Search for "radical allylation" in Full Text gives 1 result(s) in Beilstein Journal of Organic Chemistry.

Some aspects of radical chemistry in the assembly of complex molecular architectures

Béatrice Quiclet-Sire and
Samir Z. Zard

Beilstein J. Org. Chem. 2013, 9, 557–576, doi:10.3762/bjoc.9.61

processes. Keywords: amidyls; iminyls; radical allylation; radical vinylation; xanthate transfer; Introduction Natural products exhibit an astonishing diversity of molecular architectures and structural complexity. This has spurred the development of numerous synthetic strategies for the rapid assembly of

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Graphical Abstract

Scheme 1: Key radical step in the total synthesis of (–)-dendrobine.

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Scheme 2: Radical cascade in the total synthesis of (±)-13-deoxyserratine (ACCN = 1,1'-azobis(cyclohexanecarb...

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Scheme 3: Formation of the complete skeleton of (±)-fortucine.

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Scheme 4: Model radical sequence for the synthesis of quadrone.

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Scheme 5: Radical cascade using the Barton decarboxylation.

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Scheme 6: Simplified mechanism for the xanthate addition to alkenes.

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Scheme 7: Synthesis of β-lactam derivatives.

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Scheme 8: Sequential additions to three different alkenes (PhthN = phthalimido).

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Scheme 9: Key cascade in the total synthesis of (±)-matrine (43).

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Scheme 10: Synthesis of complex tetralones.

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Scheme 11: Synthesis of functionalised azaindoline and indole derivatives.

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Scheme 12: Synthesis of thiochromanones.

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Scheme 13: Synthesis of complex benzothiepinones. Conditions: 1) CF3COOH; 2) RCHO / AcOH (PMB = p-methoxybenzy...

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Scheme 14: Formation and capture of a cyclic nitrone.

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Scheme 15: Synthesis of bicyclic cyclobutane motifs.

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Scheme 16: Construction of the CD rings of steroids.

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Scheme 17: Rapid assembly of polyquinanes.

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Scheme 18: Formation of a polycyclic structure via an allene intermediate.

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Scheme 19: A polycyclic structure via the alkylative Birch reduction.

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Scheme 20: Synthesis of polycyclic pyrimidines and indoline structures.

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Scheme 21: Construction of a trans-decalin derivative.

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Scheme 22: Multiple uses of a chloroacetonyl xanthate.

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Scheme 23: A convergent route to spiroketals.

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Scheme 24: A modular approach to 3-arylpiperidines.

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Scheme 25: A convergent route to cyclopentanols and to functional allenes.

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Scheme 26: Allylation and vinylation of a xanthate and an iodide.

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Scheme 27: Vinyl epoxides as allylating agents.

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Scheme 28: Radical allylations using allylic alcohol derivatives.

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Scheme 29: Synthesis of variously substituted lactams.

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Scheme 30: Nickel-mediated synthesis of unsaturated lactams.

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Scheme 31: Total synthesis of (±)-3-demethoxy-erythratidinone.

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Scheme 32: Generation and capture of an iminyl radical from an oxime ester.

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Review

Published 18 Mar 2013

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