Highly diastereoselective formation of spirocyclic compounds via 1,5-hydrogen transfer: A total synthesis of (-)-erythrodiene

Organic Letters

Volumn 7, Issue 19, 2005, Pages 4103-4106

  Lachia, Mathilde ^a   Dénès, Fabrice ^a   Beaufils, Florent ^a   Renaud, Philippe ^a  

^a UNIVERSITY OF BERN   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CHLOROBENZENE; CYCLOHEXANE DERIVATIVE; ERYTHRODIENE; HYDROGEN; KETONE; PHENOL DERIVATIVE; SOLVENT; SPIRO COMPOUND; THIOL DERIVATIVE; THIOPHENOL;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS; TEMPERATURE;

CHLOROBENZENES; CYCLIZATION; CYCLOHEXANES; HYDROGEN; KETONES; MOLECULAR STRUCTURE; PHENOLS; SOLVENTS; SPIRO COMPOUNDS; STEREOISOMERISM; SULFHYDRYL COMPOUNDS; TEMPERATURE;

EID: 25444510868     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051426r     Document Type: Article

References (23)

1. Bagchi, A.; Oshima, Y.; Hikino, H. Tetrahedron 1990, 46, 1523.
2. Pathirana, C.; Fenical, W.; Corcoran, E.; Clardy, J. Tetrahedron Lett. 1993, 34, 3371.
3. Srikrishna, A.; Vijaykumar, D.; Reddy, T. J. Tetrahedron 1997, 53 (4), 1439.
4. Tokunaga, Y.; Yagihashi, M.; Ihara, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1997, (3), 189.
5. Tokunaga, Y.; Yagihashi, M.; Ihara, M.; Fukumoto, K. J. Chem. Soc., Chem. Commun. 1995, (9), 955.
6. Sattelkau, T.; Eilbracht, P. Tetrahedron Lett. 1998, 39, 9647.
7. Huang, H.; Forsyth, C. J. J. Org. Chem. 1995, 60, 2773.
8. Oppolzer, W.; Flachsmann, F. Tetrahedron Lett. 1998, 39, 5019.
9. Oppolzer, W.; Flachsmann, F. Helv. Chim. Acta 2001, 84, 416.
10. For a related strategy starting from an allyl sulfone, see: Deng, K. Ph.D. Thesis, etd-10252004-171707, University of Pittsburgh, 2004.
11. Beaufils, F.; Dénès, F.; Renaud, P. Org. Lett. 2004, 6, 2563.
12. Beaufils, F.; Dénès, F.; Becattini, B.; Schenk, K.; Renaud, P. Adv. Synth. Catal. 2005, in press.
13. ret = 41.56 min) are cis configured. Only the stereoselectivity of the six-membered ring is relevant for the synthesis of (-)-erythrodiene (trans relative configuration is required) and will be discussed within this paper. The second center of chirality is not controlled (dr between 1:1 and 2:1).
14. For a reviews on asymmetric synthesis using chiral lithium amide bases, see: Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1.
15. Majewski, M. Adv. Asym. Synthesis 1998, 3, 39.
16. O'Brien, P. J. Chem. Soc., Perkin Trans. 1 1998, 1439.
17. For pioneering work with lithium N,N-bis[(R)-phenylethyl]amide, see: Whitesell, J. K.; Felman, S. W. J. Org. Chem. 1980, 45, 755.
18. Simpkins, N. S. J. Chem. Soc., Chem. Commun. 1986, 88.
19. Cain, C. M.; Coumbarides, G.; Cousins, R. P. C.; Simpkins, N. S. Tetrahedron 1990, 46, 523.
20. For the effect of LiCl, see: Bunn, B. J.; Simpkins, N. S. J. Org. Chem. 1993, 58, 533.
21. Majewski, M.; Lazny, R. J. Org. Chem. 1995, 50, 6825.
22. Corey, E. J.; Bush-Petersen, J. Tetrahedron Lett. 2000, 41, 6941.
23. The enantiomeric excess was determined by GC on a chiral column: stationary phase: 50% octakis-(2,3-O-di-n-butyl-6-O-tert-butyl-dimethylsilyl)- γ-cyclodextrin in PS 086; temperature 100°C.