Reduction and Oxidation

Stannyl-Based Radical Cyclizations

A Survey of the Radical-mediated Cyclization of α-Halo Acetals of Cyclic Allyl Alcohols as a General Route to the Control of Vicinal Regio- and Stereochemistry,
  Stork, G. Bull. Soc. Chim. Fr. 1990, 675.
Stereochemistry of Intramolecular Free-radical Cyclization Reactions,
  RajanBabu, T. V. Acc. Chem. Res. 1991, 24, 139.
Radical Cyclization Reactions,
  Giese, B.; Kopping, B.; Gobel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. 1996, 48, 301-856.
Heteroatom Radical Addition-Cyclization and Its Synthetic Application,
  Naito, T. Heterocycles 1999, 50, 505-41.
Intramolecular Free Radical Conjugate Additions,
  Zhang, W. Tetrahedron 2001, 57, 7237-62.
Synthesis of Heterocycles by Radical Cyclization,
  Aldabbagh, F.; Bowman, W. R. Contemporary Org. Synth. 1997, 4, 261-80.
Synthesis of Heterocycles by Radical Cyclization,
  Bowman, W. R.; Cloonan, M. O.; Krintel, S. L. JCS Perk. I 2001, 2885-902.
Organic Syntheses through Free-radical Annulations and Related Cascade Sequences,
  McCarroll, A. J.; Walton, J. C. JCS Perk. I 2001, 3215-29.
5-Endo-Trig Radical Cyclizations,
  Ishibashi, H.; Sato, T.; Ikeda, M. Synthesis 2002, 695-713.
Formation of Five-and Six-Membered Heterocyclic Rings by Radical Cyclization,
  Majumdar, K. C.; Basu, P. K. Heterocycles 2002, 57, 2413-39.
Formation of Five- and Six-Membered Heterocyclic Rings Under Radical Cyclization Conditions,
  Majumdar, K. C.; Basu, P. K.; Mukhopadhyay, P. P. Tetrahedron 2004, 60, 6239-78. Tetrahedron 2007, 63, 793-826.

  The intermediate radicals generated by abstraction of a halogen or other X group with R3Sn· can also be trapped by double and triple bonds to forn new C-C bonds. These radical cyclizations work most efficiently when 5-membered rings are being formed. It is often necessary to carefully control concentrations and reaction conditions to avoid capture of the intermediate radicals by R3Sn-H to form reduction rather than cyclization products.


 

Tandem Radical Cyclization Approach to Hirsutene: D. P. Curran, D. M. Rakiewicz J. Am. Chem. Soc. 1985, 107, 1448.

 

Vinyl Radicals - Merrilactone: Birman, V. B.; Danishefsky, S. J. J. Am. Chem. Soc. 2002, 124, 2080-2081

 

Radical Cyclization to Achieve cis-Hydroxyalkylation

Stork, Kahn J. Am. Chem. Soc. 1985, 107, 500.

 

14-Deoxyisoamijiol: Majetich, G.; Song, J. S.; Ringold, C.; Nemeth, G. A. Tetrahedron Lett. 1990, 31, 2239

 

Acyl Radicals from Acyl Selenides


 

Spongian-16-one: Pattenden, Roberts Tetrahedron Lett. 1996, 37, 4191.


 

Generation of Iminoyl Radicals - Synthesis of Camptothecin: Curran, Ko, Josien Angew. Chem., Int. Ed. Engl. 1995, 34, 2683.