New strategy for the stereocontrolled construction of decalins and fused polycycles via a tandem diels - Alder ring-opening sequence

Journal of Organic Chemistry

Volumn 61, Issue 23, 1996, Pages 7994-7995

  Lautens, Mark ^a   Fillion, Eric ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000953702     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961635c     Document Type: Article

References (35)

1. The terms pincer, tandem, and domino have been used to describe multistage Diels-Alder reactions. For examples, see recent reviews on Diels - Alder cycloadditions: (a) Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137. (b) Winkler, J. D. Chem. Rev. 1996, 96, 167. (c) Ho, T.-L. Tandem Organic Reactions; Wiley: New York, 1992.
2. The terms pincer, tandem, and domino have been used to describe multistage Diels-Alder reactions. For examples, see recent reviews on Diels - Alder cycloadditions: (a) Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137. (b) Winkler, J. D. Chem. Rev. 1996, 96, 167. (c) Ho, T.-L. Tandem Organic Reactions; Wiley: New York, 1992.
3. The terms pincer, tandem, and domino have been used to describe multistage Diels-Alder reactions. For examples, see recent reviews on Diels - Alder cycloadditions: (a) Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137. (b) Winkler, J. D. Chem. Rev. 1996, 96, 167. (c) Ho, T.-L. Tandem Organic Reactions; Wiley: New York, 1992.
4. (a) For the first use of the term "pincer" Diels - Alder, see: Paquette, L. A.; Wyvratt, M. J.; Berk, H. C., Moerck, R. E. J. Am. Chem. Soc. 1978, 100, 5845.
5. (b) Paquette, L. A.; Balogh, D. W. J. Am. Chem. Soc. 1982, 104, 774.
6. (a) Diels, O.; Alder, K. Justus Liebigs Ann. Chem. 1931, 490, 243.
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15. (j) For historical information on this reaction, see: Slee, J. D.; LeGoff, E. J. Org. Chem. 1970, 35, 3897.
16. (k) McCulloch, A. W.; Smith, D. G.; Mclnnes, A. G. Can. J. Chem. 1974, 52, 1013.
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23. (r) Russell, R. A.; Longmore, R. W.; Weerasuria, K. D. V.; Warrener, R. N. Aust. J. Chem. 1991, 44, 1341.
24. (s) During the course of our study, the synthesis of a dioxapentacycle by a simultaneous double Diels-Alder addition of a tethered bis-furan with a bis-dienophile has been reported; see: Marchionni, C.; Vogel, P.; Roversi, P. Tetrahedron Lett. 1996, 37, 4149.
25. (a) For a recent review on the ring opening of oxabicyclic systems, see: Woo, S.; Keay, B. Synthesis 1996, 669.
26. (b) For a review of our previous work and historical information on this reaction, see: Lautens, M. Synlett 1993, 177.
27. (c) Lautens, M.: Chiu, P.; Ma, S.; Rovis, T. J. Am. Chem. Soc. 1995, 117, 532.
28. For a recent review on aromatic heterocycles as intermediates in synthesis, see: Shipman, M. Contemp. Org. Synth. 1995, 2, 1.
29. Some authors refer to this stereochemistry as endo-endo.
30. 1H NMR spectrum of the mother liquor indicated the presence of the exo-endo cycloadduct, which did not crystallize out of the solution. The oxanorbornadiene type intermediate 1 was the major component present in the reaction mixture,
31. (b) For a detailed study on the Diels-Alder reaction between furan and dimethyl acetylenedicarboxylate, see: McCulloch, A. W.; Smith, D. G.; Mclnnes, A. G. Can. J. Chem. 1973, 51, 4125.
32. (c) Visnick, M.; Battiste, M. A. J. Chem. Soc., Chem. Commun. 1985, 1621.
33. The bis-furan 3 was prepared in 38% yield by treating 1,3-diiodopropane with 2-lithiofuran.
34. 1H NMR spectrum of the mother liquor showed the absence of the oxanorbonadiene intermediate, which suggests that the rate of the intramolecular cycloaddition is much faster than the intermolecular one. Also, no trace of the exo-endo cycloadduct was observed in the reaction mixture.
35. The hydroxy group had to be protected in order for the reductive ring-opening reaction to occur.