Base-catalyzed endo-mode cyclization of allenes: Easy preparation of five- to nine-membered oxacycles

Journal of Organic Chemistry

Volumn 69, Issue 20, 2004, Pages 6867-6873

  Mukai, Chisato ^a   Ohta, Masaru ^a   Yamashita, Haruhisa ^a   Kitagaki, Shinji ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CATALYSIS; CHEMICAL BONDS; REACTION KINETICS;

ALLENES; CYCLIZATION; RING-CLOSING REACTIONS; SIDE CHAINS;

OLEFINS;

3 DIETHOXYPHOSPHINYL 2 METHYL 4,5,8,9 TETRAHYDROOXONIN; 3 DIETHOXYPHOSPHINYL 3,4 PENTADIEN 1 OL; 3 DIPHENYLPHOSPHINYL 2 METHYL 4,5 DIHYDROFURAN; 3 DIPHENYLPHOSPHINYL 2 METHYL 4,5,6,7 TETRAHYDROXEPIN; 3 DIPHENYLPHOSPHINYL 2 METHYL 4,5,8,9 TETRAHYDROOXONIN; 5 DIPHENYLPHOSPHINYL 6 METHYL 3,4 DIHYDRO 2H PYRAN; 7 DIETHOXYPHOSPHINYL 8 METHYL 3,4,5,6 TETRAHYDRO 2H OXOCIN; ALCOHOL DERIVATIVE; ALLENE DERIVATIVE; FUNCTIONAL GROUP; PHOSPHINE OXIDE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; PROPARGYL ALCOHOL DERIVATIVE; SULFOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CYCLIZATION; RING CLOSING METATHESIS;

EID: 4644319585     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0488614     Document Type: Article

References (29)

1. (a) Moore, R. E. In Marine Natural Products: Chemical and Biological Perspectives; Scheuer, P. J., Ed.; Academic Press: New York, 1978; Vol. 1, pp 43-124.
2. (b) Faulkner, D. J. Nat. Prod. Rep. 1986, 3, 1-33.
3. (c) Yasumoto, T.; Murata, M. Chem. Rev. 1993, 93, 1897-1909.
4. (d) Faulkner, D. J. Nat. Prod. Rep. 1996, 13, 75-125.
5. Mukai, C.; Yamashita, H.; Hanaoka, M. Org. Lett. 2001, 3, 3385-3387.
6. Horner, L.; Binder, V. Liebigs Ann. Chem. 1972, 757, 33-68.
7. Parsons reported an exo-mode ring-closing reaction of allenyl sulfoxide derivatives; see: (a) Pairaudeau, G.; Parsons, P. J.; Underwood, J. M. J. Chem. Soc., Chem. Commun. 1987, 1718-1720. (b) Gray, M.; Parsons, P. J.; Neary, A. P. Synlett 1992, 597-598. (c) Gray, M.; Parsons, P. J.; Neary, A. P. Synlett 1993, 281-282. (d) Parsons, P. J.; Stefinovic, M. Synlett 1993, 931-932. (e) Edwards, N.; Macritchie, J. A.; Parsons, P. J.; Drew, M. G. B.; Jahans, A. W. Tetrahedron 1997, 53, 12651-12660.
8. Parsons reported an exo-mode ring-closing reaction of allenyl sulfoxide derivatives; see: (a) Pairaudeau, G.; Parsons, P. J.; Underwood, J. M. J. Chem. Soc., Chem. Commun. 1987, 1718-1720. (b) Gray, M.; Parsons, P. J.; Neary, A. P. Synlett 1992, 597-598. (c) Gray, M.; Parsons, P. J.; Neary, A. P. Synlett 1993, 281-282. (d) Parsons, P. J.; Stefinovic, M. Synlett 1993, 931-932. (e) Edwards, N.; Macritchie, J. A.; Parsons, P. J.; Drew, M. G. B.; Jahans, A. W. Tetrahedron 1997, 53, 12651-12660.
9. Parsons reported an exo-mode ring-closing reaction of allenyl sulfoxide derivatives; see: (a) Pairaudeau, G.; Parsons, P. J.; Underwood, J. M. J. Chem. Soc., Chem. Commun. 1987, 1718-1720. (b) Gray, M.; Parsons, P. J.; Neary, A. P. Synlett 1992, 597-598. (c) Gray, M.; Parsons, P. J.; Neary, A. P. Synlett 1993, 281-282. (d) Parsons, P. J.; Stefinovic, M. Synlett 1993, 931-932. (e) Edwards, N.; Macritchie, J. A.; Parsons, P. J.; Drew, M. G. B.; Jahans, A. W. Tetrahedron 1997, 53, 12651-12660.
10. Parsons reported an exo-mode ring-closing reaction of allenyl sulfoxide derivatives; see: (a) Pairaudeau, G.; Parsons, P. J.; Underwood, J. M. J. Chem. Soc., Chem. Commun. 1987, 1718-1720. (b) Gray, M.; Parsons, P. J.; Neary, A. P. Synlett 1992, 597-598. (c) Gray, M.; Parsons, P. J.; Neary, A. P. Synlett 1993, 281-282. (d) Parsons, P. J.; Stefinovic, M. Synlett 1993, 931-932. (e) Edwards, N.; Macritchie, J. A.; Parsons, P. J.; Drew, M. G. B.; Jahans, A. W. Tetrahedron 1997, 53, 12651-12660.
11. Parsons reported an exo-mode ring-closing reaction of allenyl sulfoxide derivatives; see: (a) Pairaudeau, G.; Parsons, P. J.; Underwood, J. M. J. Chem. Soc., Chem. Commun. 1987, 1718-1720. (b) Gray, M.; Parsons, P. J.; Neary, A. P. Synlett 1992, 597-598. (c) Gray, M.; Parsons, P. J.; Neary, A. P. Synlett 1993, 281-282. (d) Parsons, P. J.; Stefinovic, M. Synlett 1993, 931-932. (e) Edwards, N.; Macritchie, J. A.; Parsons, P. J.; Drew, M. G. B.; Jahans, A. W. Tetrahedron 1997, 53, 12651-12660.
12. Dai described an exo-mode cyclization of the allenyl sulfone derivatives resulting in a formation of the five-membered oxacycles: Dai, W.-M.; Lee, M. Y. H. Tetrahedron 1998, 54, 12497-12512.
13. (a) Nicolaou, K. C.; Maligres, P.; Shin, J,; de Leon, E.; Rideout, D. J. Am. Chem. Soc. 1990, 112, 7825-7826.
14. (b) Curtin, M. L.; Okamura, W. H. J. Org. Chem. 1990, 55, 5278-5287.
15. A similar endo-mode ring-closing reaction of trisubstituted allenylphosphine oxides, leading to the dihydrofuran skeleton, has been reported: Pravia, K.; White, R.; Fodda, R.; Maynard, D. F. J. Org. Chem. 1996, 61, 6031-6032.
16. Brel reported an exo-mode cyclization of the allenylphosphonate derivatives leading to a furan framework: Brel, V. K. Synthesis 2001, 1539-1545.
17. tBuOH at 60°C.
18. Brown, C. A.; Ahuja, V. K. J. Org. Chem. 1973, 38, 2226-2230.
19. Hayashi, N.; Noguchi, H.; Tsuboi, S. Tetrahedron 2000, 56, 7123-7137.
20. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 3769-3772.
21. Schultz, H. S.; Freyermuth, H. B.; Buc, S. R. J. Org. Chem. 1963, 28, 1140-1142.
22. The newly formed product was identified as 17b.
23. The stereochemistry of compound 17 was undetermined. On the basis of molecular model considerations, we tentatively assumed that the relative stereochemistry between the acetyl and vinyl groups was cis.
24. For [3,3]-sigmatropic rearrangement of the acyclic vinyl ether derivatives, which have an allyl moiety with an electron-withdrawing group, see: (a) Cookson, R. C.; Gopalan, R. J. Chem. Soc., Chem. Commun. 1978, 608. (b) Denmark, S. E.; Harmata, M. A. J. Am. Chem. Soc. 1982, 104, 4972-4974. (c) Denmark, S. E.; Marlin, J. E. J. Org. Chem. 1991, 56, 1003-1013.
25. For [3,3]-sigmatropic rearrangement of the acyclic vinyl ether derivatives, which have an allyl moiety with an electron-withdrawing group, see: (a) Cookson, R. C.; Gopalan, R. J. Chem. Soc., Chem. Commun. 1978, 608. (b) Denmark, S. E.; Harmata, M. A. J. Am. Chem. Soc. 1982, 104, 4972-4974. (c) Denmark, S. E.; Marlin, J. E. J. Org. Chem. 1991, 56, 1003-1013.
26. For [3,3]-sigmatropic rearrangement of the acyclic vinyl ether derivatives, which have an allyl moiety with an electron-withdrawing group, see: (a) Cookson, R. C.; Gopalan, R. J. Chem. Soc., Chem. Commun. 1978, 608. (b) Denmark, S. E.; Harmata, M. A. J. Am. Chem. Soc. 1982, 104, 4972-4974. (c) Denmark, S. E.; Marlin, J. E. J. Org. Chem. 1991, 56, 1003-1013.
27. Staab, H. A.; Meissner, U. E.; Weinacht, W.; Gensler, A. Chem. Ber. 1979, 112, 3895-3906,
28. Schow, S. R.; McMorris, T. C. J. Org. Chem. 1979, 44, 3760-3765.
29. Both isomers 24b and 24b′ could be isolated by chromatography. Compounds 24b and 24b′ were independently exposed to the ring-closing conditions to give a similar mixture of 24b and 24b′ in a ratio of ca. 2:1.