Tributyltin Hydride–Mediated Synthesis of Bicyclic Carbocycles Initiated by Et₃B/O₂

REFERENCES

• (a) Heathcock , C. H. In Total Synthesis of Natural Products ; T. Apsimon (Ed.); Wiley : New York , 1973 ; vol. 2 , p. 197 ; vol. 5, pp. 383–384, 405–423; (b) Shibasaki, M.; Takahashi, A.; Aoki, J.; Sato, H.; Nasita, S. Synthesis of cis-bicyclo[4.3.0]non-2-ene. Chem. Pharm. Bull. 1989, 37, 1647–1649 .
   Google Scholar
• For reviews in this field see (a) Olliver , C. ; Renaud , P. Organoboranes as a source of radicals . Chem. Rev. 2001 , 101 , 3415 – 3434 ; (b) Yorimitsu, H.; Oshima, K. In Radicals in Organic Synthesis; P. Renaud and M. Sibi (Eds.); Wiley-VCH: Weinheim, 2001; vol. 1, pp. 11–27; (c) Sibi, M. P.; Rheault, T. R. In Radicals in Organic Synthesis; P. Renaud, M. P. Sibi (Eds.); Wiley-VCH: Weinheim, 2001; vol. 1, pp. 461–478 .
   PubMedGoogle Scholar
• Prakash , C. ; Mohanakrishnan , A. K. Synthesis of angularly fused carbocycles via tandem radical cyclization of α-carbonyl radicals . Eur. J. Org. Chem. 2008 , 1535 – 1543 .
   Google Scholar
• Brady , F. S. ; Singh , P. M. ; Janso , E. J. ; Clardy , J. Guanacastepene, a fungal-derived diterpene antibiotic with a new carbon skeleton . J. Am. Chem. Soc. 2001 , 122 , 2116 – 2117 .
   Google Scholar
• Hirotani , M. ; Masuda , M. ; Sukemori , A. ; Hirotani , S. ; Sato , N. ; Yoshikawa , T. Agariblazeispirol C from the cultured mycelia of the fungus, Agaricus blazei, and the chemical conversion of blazeispirol A . Tetrahedron 2005 , 61 , 189 – 194 .
   Google Scholar
• Kihara , N. ; Ollivier , C. ; Renaud , P. Efficient radical oxygenation of α-iodo carboxylic acid derivatives . Org. Lett. 1999 , 1 , 1419 – 1422 .
   Google Scholar
• Mohanakrishnan , A. K. ; Prakash , C. ; Ramesh , N. A simple iodination protocol via in situ–generated ICl using NaI/FeCl3 . Tetrahedron 2006 , 62 , 3242 – 3247 .
   Web of Science ®Google Scholar
• (a) Dauben , W. G. ; Michno , D. M. Direct oxidation of tertiary allylic alcohols: A simple and effective method for alkylative carbonyl transposition. J. Org. Chem. 1977, 42, 682–685; (b) Ito , Y. ; Hirao , T. ; Saegusa , T. Synthesis of α,β-unsaturated carbonyl compounds by palladium (II)–catalysed dehydrosilylation of silyl enol ethers. J. Org. Chem. 1978, 43, 1011–1013; (c) Larock , R. C. ; Hightower , T. R. ; Kraus , G. A. ; Hahn , P. ; Zheng , D. A simple, effective, new, palladium-catalyzed conversion of enol silanes to enones and enals. Tetrahedron Lett. 1995, 36, 2423–2426.
   Web of Science ®Google Scholar
• (a) Sha , C.-K. ; Young , J.-J. ; Jean , T.-S. Synthesis of α-iodo ketones . J. Org. Chem. 1987 , 52 , 3919 – 3920 .
   Google Scholar
• (a) Sha , C.-K. ; Jean , T.-S. ; Wang , D.-C. Intramolecular radical cyclization of silylacetylenic or olefinic α-iodo ketones: Application to the total synthesis of (±)-modhephene . Tetrahedron Lett. 1990 , 31 , 3745 – 3748 ; (b) Sha , C.-K. ; Jean , T.-S. ; Yau , N.-T. ; Huang , S.-J. ; Chiu , R.-T. ; Young , J.-F. ; Lih , S.-H. ; Tseng , W.-H. α-Carbonyl radicals for total synthesis of natural products . Pure Appl. Chem. 1996 , 68 , 687 – 689 .
   Google Scholar
• Rodrĭguez , J. R. ; Castedo , L. ; Macareňas , J. L. Synthesis of eight- and nine-membered carbocycles through a ring-closing metathesis/ring fragmentation strategy: A rapid and versatile approach to bicyclo[6.4.0]- and bicyclo[7.4.0]alkene ring systems . Chem. Eur. J. 2002 , 8 , 2923 – 2930 .
   PubMedGoogle Scholar
• Stealey , M. A. ; Shone , R. L. ; Miyano , M. A convenient synthesis of 2-alkyl-mono-o-alkylated and 2-alkyl resorcinols . Synth. Commun. 1990 , 20 , 1869 – 1876 .
   Web of Science ®Google Scholar