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
Graphical Abstract
Scheme 1: Key radical step in the total synthesis of (–)-dendrobine.
Scheme 2: Radical cascade in the total synthesis of (±)-13-deoxyserratine (ACCN = 1,1'-azobis(cyclohexanecarb...
Scheme 3: Formation of the complete skeleton of (±)-fortucine.
Scheme 4: Model radical sequence for the synthesis of quadrone.
Scheme 5: Radical cascade using the Barton decarboxylation.
Scheme 6: Simplified mechanism for the xanthate addition to alkenes.
Scheme 7: Synthesis of β-lactam derivatives.
Scheme 8: Sequential additions to three different alkenes (PhthN = phthalimido).
Scheme 9: Key cascade in the total synthesis of (±)-matrine (43).
Scheme 10: Synthesis of complex tetralones.
Scheme 11: Synthesis of functionalised azaindoline and indole derivatives.
Scheme 12: Synthesis of thiochromanones.
Scheme 13: Synthesis of complex benzothiepinones. Conditions: 1) CF3COOH; 2) RCHO / AcOH (PMB = p-methoxybenzy...
Scheme 14: Formation and capture of a cyclic nitrone.
Scheme 15: Synthesis of bicyclic cyclobutane motifs.
Scheme 16: Construction of the CD rings of steroids.
Scheme 17: Rapid assembly of polyquinanes.
Scheme 18: Formation of a polycyclic structure via an allene intermediate.
Scheme 19: A polycyclic structure via the alkylative Birch reduction.
Scheme 20: Synthesis of polycyclic pyrimidines and indoline structures.
Scheme 21: Construction of a trans-decalin derivative.
Scheme 22: Multiple uses of a chloroacetonyl xanthate.
Scheme 23: A convergent route to spiroketals.
Scheme 24: A modular approach to 3-arylpiperidines.
Scheme 25: A convergent route to cyclopentanols and to functional allenes.
Scheme 26: Allylation and vinylation of a xanthate and an iodide.
Scheme 27: Vinyl epoxides as allylating agents.
Scheme 28: Radical allylations using allylic alcohol derivatives.
Scheme 29: Synthesis of variously substituted lactams.
Scheme 30: Nickel-mediated synthesis of unsaturated lactams.
Scheme 31: Total synthesis of (±)-3-demethoxy-erythratidinone.
Scheme 32: Generation and capture of an iminyl radical from an oxime ester.
