Thallium(III)-Mediated Ring Contraction of cis-Octalins: An Approach for the Diastereoselective Construction of the nor-Bakkane Skeleton

Helena M. C. Ferraz; Tiago O. Vieira; Luiz F. Silva

doi:10.1055/s-2006-942500

PAPER

Thallium(III)-Mediated Ring Contraction of cis-Octalins: An Approach for the Diastereoselective Construction of the nor-Bakkane Skeleton

Helena M. C. Ferraz*, Tiago O. Vieira, , Jr Luiz F. Silva
Instituto de Química, Universidade de São Paulo, CP 26077, CEP 05513-970, São Paulo SP, Brazil
Fax: +55(11)8155579; e-Mail: hmferraz@iq.usp.br;

Abstract

All articles of this category

Abstract

A new approach for the diastereoselective synthesis of cis-hydrindanes bearing important structural features of the bakkane skeleton is described. The key step in such a sequence is a thallium trinitrate mediated oxidative rearrangement of cis-octalins. The ring-contraction products thus obtained were elaborated in a diastereoselective fashion into hydrindanes bearing a quaternary center.

Keywords

bakkanes - ring contraction - thallium(III) - hydrindanes - oxidative rearrangement

Full Text

References

1a Abe N. Onoda R. Shirahata K. Kato T. Woods MC. Kitahara Y. Tetrahedron Lett. 1968, 369

1b Naya K. Takagi I. Hayashi M. Nakamura S. Kobayashi M. Katsumura S. Chem. Ind. (London) 1968, 318

2 For a review concerning the chemistry of bakkanes, see: Silva LF. Synthesis 2001, 671

For examples, see:

3a Jamieson GR. Reid EH. Turner BP. Jamieson AT. Phytochemistry 1976, 15: 1713

3b Kano K. Hayashi K. Mitsuhashi H. Chem. Pharm. Bull. 1982, 30: 1198

3c Wu T.-S. Kao M.-S. Wu P.-L. Lin F.-W. Shi L.-S. Liou M.-J. Li C.-Y. Chem. Pharm. Bull. 1999, 47: 375

For examples, see:

4a Nawrot J. Bloszyk E. Harmatha J. Novotný L. J. Appl. Entomol. 1984, 98: 394

4b Nawrot J. Harmatha J. Novotn L. Biochem. Syst. Ecol. 1984, 12: 99

5 Wu T.-S. Kao M.-S. Wu P.-L. Lin F.-W. Shi L.-S. Teng C.-M. Phytochemistry 1999, 52: 901

6 Liao C.-H. Ko F.-N. Wu T.-S. Teng C.-M. J. Pharm. Pharmacol. 1997, 49: 1248

7 Reddy DS. Org. Lett. 2004, 6: 3345

8a Back TG. Nava-Salgado VO. Payne JE. J. Org. Chem. 2001, 66: 4361

8b Back TG. Payne JE. Org. Lett. 1999, 1: 663

9a Srikrishna A. Reddy TJ. Arkivoc 2001, (viii): 9

9b Srikrishna A. Nagaraju S. Venkateswarlu S. Hiremath US. Reddy TJ. Venugopalan P. J. Chem. Soc., Perkin Trans. 1 1999, 2069

9c Hayashi K. Nakamura H. Mitsuhashi H. Chem. Pharm. Bull. 1973, 21: 2806

10 Mori K. Matsushima Y. Synthesis 1995, 845

11a Evans DA. Sims CL. Tetrahedron Lett. 1973, 4691

11b Evans DA. Sims CL. Andrews GC. J. Am. Chem. Soc. 1977, 99: 5453

For some leading references, see:

12a Brocksom TJ. Coelho F. Depres JP. Greene AE. de Lima MEF. Hamelin O. Hartmann B. Kanazawa AM. Wang YY. J. Am Chem. Soc. 2002, 124: 15313

12b Hamelin O. Wang Y. Depres JP. Greene AE. Angew. Chem. Int. Ed. 2000, 39: 4314

12c Hamelin O. Deprés J.-P. Greene AE. Tinant B. Declercq J.-P. J. Am. Chem. Soc. 1996, 118: 9992

12d Greene AE. Deprés J.-P. Coelho F. Brocksom TJ. J. Org. Chem. 1985, 50: 3943

12e

For other papers, see, for example: ref. 2 and ref. 12a.

13 Kabbe H.-J. Justus Liebigs Ann. Chem. 1962, 656: 204

14a Lee JB. Price MJ. Tetrahedron Lett. 1962, 1155

14b Lee JB. Price MJ. Tetrahedron 1964, 20: 1017

15 Anderson CB. Winstein S. J. Org. Chem. 1963, 28: 605

For some reviews concerning thallium(III), see:

16a McKillop A. Taylor EC. In Comprehensive Organometallic Chemistry Vol. 7: Wilkinson G. Pergamon Press; New York: 1982. p.465

16b Ferraz HMC. Silva LF. Vieira Tde O. Synthesis 1999, 2001

16c McKillop A. Taylor EC. In Organic Synthesis by Oxidation with Metal Compounds Mijs WJ. De Jonge CRHI. Plenum; New York: 1986. p.695

17a For a review concerning thallium(III)-mediated ring-contraction reactions, see: Ferraz HMC. Silva LF. Quim. Nova 2000, 23: 216

17b For a review concerning ring contraction reactions, see: Silva LF. Tetrahedron 2002, 58: 9137

18 Ferraz HMC. Silva LF. Tetrahedron 2001, 57: 9939

19 Ferraz HMC. Silva LF. Vieira TO. Tetrahedron 2001, 57: 1709

20 Silva LF. Sousa RMF. Ferraz HMC. Aguilar AM. J. Braz. Chem. Soc. 2005, 16: 1160

21a Ferraz HMC. Aguilar AM. Silva LF. Synthesis 2003, 1031

21b Ferraz HMC. Aguilar AM. Silva LF. Tetrahedron 2003, 59: 5817

22 Ferraz HMC. Silva LF. J. Org. Chem. 1998, 63: 1716

23 Ferraz HMC. Silva LF. J. Braz. Chem. Soc. 2001, 12: 548

24 2-Methylcyclohex-2-enone was prepared in two steps (bromination followed by dehydrohalogenation) from 2-methylcyclohexanone, in 68% yield: Hua DH. Chen Y. Sin H.-S. Maroto MJ. Robinson PD. Newell SW. Perchellet EM. Ladesich JB. Freeman JA. Perchellet J.-P. Chiang PK. J. Org. Chem. 1997, 62: 6888

25 Nagakura I. Ogata H. Ueno M. Kitahara Y. Bull. Chem. Soc. Jpn. 1975, 48: 2995

26 Fringuelli F. Pizzo F. Taticchi A. Halls TDJ. Wenkert E. J. Org. Chem. 1982, 47: 5056

27 Angell EC. Fringuelli F. Pizzo F. Taticchi A. Wenkert E. J. Org. Chem. 1988, 53: 1224

28 McKillop A. Hunt JD. Kienzle F. Bigham E. Taylor EC. J. Am. Chem. Soc. 1973, 95: 3635

29 Abley P. Byrd JE. Halpern J. J. Am. Chem. Soc. 1973, 95: 2591

30 Sekizaki H. Ito M. Inoue S. Bull. Chem. Soc. Jpn. 1978, 51: 2439

31 Heathcock CH. Ratcliffe R. Van J. J. Org. Chem. 1972, 37: 1796

32 Ratcliffe BE. Heathcock CH. J. Org. Chem. 1972, 37: 531

33

The X-ray data have been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition number CCDC 605577.