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Volumn 109, Issue 25, 1987, Pages 7908-7910

A Stereoselective, Palladium-Catalyzed Route to 4-Oxygenated 5-Alkylidenecyclopentenones and 3-Oxyeenated 2-Alkylideneindanones

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EID: 0001404234     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00259a064     Document Type: Article
Times cited : (100)

References (15)
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    • Baker, B. J.; Okuda, R. K.; Yu, P. T. K.; Scheuer, P. J. J. Am. Chem. Soc. 1985, 108, 2976–2877. Nagaoka, H.; Miyaoka, H.; Miyakoshi, Y.; Yamada, Y. J. Chem. Soc., Chem. Commun. 1986, 108, 5019–5021.
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    • Tius, M. A.; Astrab, D. P. Tetrahedron Lett. 1984, 1539. Pohmakotr, M.; Chancharunee, S. Tetrahedron Lett. 1984, 4141. Siwapinyoyos, T.; Thebtaranonth, Y. J. Org. Chem. 1982, 47, 598. (e) Block, E.; Wall, A.; Zubieta, J. J. Am. Chem. Soc. 1985, 107, 1783–1784. (f) Negishi, E. I. ; Miller, J. A. J. Am. Chem. Soc. 1983, 105, 6761. (g) Tour, J. M.; Negishi, E. I. J. Am. Chem. Soc. 1985, 107, 8289. (h) Williams, D. R.; Abbaspour, A.; Jacobson, R. M. Tetrahedron Lett. 1981, 3565–3568. (i) Karlsson, J. O.; Nguyen, N. V.; Foland, L. D.; Moore, H. W. J. Am. Chem. Soc. 1985, 107, 3392–3393, (j) Ramaiah, M. Synthesis 1984, 529–570. Specific syntheses of the alkylidene cyclopentenone natural products. Methylenomycin A and B: (a) Scarborough, R. M., Jr.; Toder, B. H.; Smith, A. B., III. J. Am. Chem. Soc. 1980, 102, 3904–3913. Jernow, J.; Tautz, W.; Rosen, P.; Blout, J. F. J. Org. Chem. 1979, 44, 4210 and 4212. Koreeda, M.; Chen, Y. P. L. Tetrahedron Lett. 1981, 15. Newton, R. F.; Reynolds, D. P.; Eyre, T. Synth. Commun, 1981, 11, 527–532. (e) Takahashi, Y.; Kosugi, H.; Uda, H. J. Chem. Soc., Chem. Commun. 1982, 496–497. (f) Billington, D. C.; Pauson, P. L. Organometallics 1982, 1, 1560–1561. (g) Strunz, B. M.; Lal G. S. Can. J. Chem. 1982, 60, 2525–2530. (h) Doutheau, A.; Sartoretti, J.; Gore, J. Tetrahedron 1983, 39, 3059–3065. (i) Mikolajczyk, M.; Balczewski, P. Synthesis 1984, 691–694. (j) Cameron, A. G.; Hewson, A. T.; Osammor, M. Tetrahedron Lett. 1984, 2267–2270. (k) Takahashi, Y.; Isobe, K.; Hagiwara, H.; Kosugi, H.; Uda, H., J. Chem. Soc., Chem. Commun. 1981, 714–715. (1) Boschelli, D.; Scarborough, R. M., Jr.; Smith, A. B., III. Tetrahedron Lett. 1981, 19–22. (m) Tius, M. A.; Astrab, D. P.; Fauq, A. H.; Ousset, J. B. ; Trehan, S. J. Am. Chem. Soc. 1986, 108, 3438–3442. (n) Reference 9c. d, and f. Pentenomycin: (a) Verlaak, J. M. J.; Klunder, A. J. H.; Zwanenburg, B. Tetrahedron Lett. 1982, 5436–5466. Klunder, A. J. H.; Houwen-Claasen, A. A. M.; Kooy, M. G.; Zwanenburg, B. Tetrahedron Lett. 1987, 1329–1332. Xanthocidin: Smith. A. B., III.; Boschelli, D. J. Org. Chem. 1983, 48, 1217–1226. Sarkomycin: (a) Toki, K. Bull. Chem. Soc. Jpn. 1957, 30, 450. Shemyakin, M. M.; Ravdel, G. A.; Chaman, Ye. S.; Shevtsov, Y. B.; Vinogradova, Ye. I. Chem. Ind. 1957, 1320. Boeckmann, R., Jr.; Naegely, P. C.; Arthur, S. D. J. Org. Chem. 1980, 45, 752. Kobayashi, Y.; Tsuji, J. Tetrahedron Lett. 1981, 4295. (e) Barreiro, E. J. Tetrahedron Lett. 1982, 3605. (f) Wexler, B. A.; Toder, B. H.; Minaskanian, G.; Smith, A. B., III. J. Org. Chem. 1982, 23, 3333. (g) Marx, J. N.; Minaskanian, G. J. J. Org. Chem. 1982, 47, 3306. (h) Hewson, A. T.; McPherson, D. T. Tetrahedron Lett. 1983, 647. (i) Govindan, S. V.; Hudlicky, T.; Koszyk, F. J. Org. Chem. 1983, 28, 3581. (j) Kodpinid, M. M.; Siwapinyoyos, T.; Thebtaranonth, Y. J. Am. Chem. Soc. 1984, 106, 4862. Clavulones: (a) Corey, E. J.; Mehrotra, M. M. J. Am. Chem. Soc. 1984, 106, 3384. Shibasaki, M.; Ogawa, Y. Tetrahedron Lett. 1985, 3841–3844. Hashimoto, S.; Arai, Y.; Hamanaka, H. Tetrahedron Lett. 1985, 2679–2682. Nagaoka, H.; Miyakoshi, T.; Kasuga, J. I. ; Yamada, Y. Tetrahedron Lett. 1985, 5053–5056. Chlorovulones: Nagaoka, H.; Iguchi, K.; Miyakoshi, T.; Yamada, N.; Yamada, Y. Tetrahedron Lett. 1986, 223–226 (1986). Puna-glandins: (a) Nagaoka, H.; Miyaoka, H.; Miyakoshi, Y.; Yamada, Y. J. Am. Chem. Soc. 1986,108, 5019–5021. Suzuki, M.; Morita, Y.; Yanagisawa, A.; Noyori, R.; Baker, B. J., Jr.; Scheuer, P. J. J. Am. Chem. Soc. 1986, 108, 5021–5022. Sasai, H.; Shibasaki, M. Tetrahedron Lett. 1987, 333–337.
    • Approaches to alkylidene cyclopentenones: (a) Katsin, N.; R. Ikan, R. Synth. Commun. 1977, 7, 185–188. Tius, M. A.; Astrab, D. P. Tetrahedron Lett. 1984, 1539. Pohmakotr, M.; Chancharunee, S. Tetrahedron Lett. 1984, 4141. Siwapinyoyos, T.; Thebtaranonth, Y. J. Org. Chem. 1982, 47, 598. (e) Block, E.; Wall, A.; Zubieta, J. J. Am. Chem. Soc. 1985, 107, 1783–1784. (f) Negishi, E. I. ; Miller, J. A. J. Am. Chem. Soc. 1983, 105, 6761. (g) Tour, J. M.; Negishi, E. I. J. Am. Chem. Soc. 1985, 107, 8289. (h) Williams, D. R.; Abbaspour, A.; Jacobson, R. M. Tetrahedron Lett. 1981, 3565–3568. (i) Karlsson, J. O.; Nguyen, N. V.; Foland, L. D.; Moore, H. W. J. Am. Chem. Soc. 1985, 107, 3392–3393, (j) Ramaiah, M. Synthesis 1984, 529–570. Specific syntheses of the alkylidene cyclopentenone natural products. Methylenomycin A and B: (a) Scarborough, R. M., Jr.; Toder, B. H.; Smith, A. B., III. J. Am. Chem. Soc. 1980, 102, 3904–3913. Jernow, J.; Tautz, W.; Rosen, P.; Blout, J. F. J. Org. Chem. 1979, 44, 4210 and 4212. Koreeda, M.; Chen, Y. P. L. Tetrahedron Lett. 1981, 15. Newton, R. F.; Reynolds, D. P.; Eyre, T. Synth. Commun, 1981, 11, 527–532. (e) Takahashi, Y.; Kosugi, H.; Uda, H. J. Chem. Soc., Chem. Commun. 1982, 496–497. (f) Billington, D. C.; Pauson, P. L. Organometallics 1982, 1, 1560–1561. (g) Strunz, B. M.; Lal G. S. Can. J. Chem. 1982, 60, 2525–2530. (h) Doutheau, A.; Sartoretti, J.; Gore, J. Tetrahedron 1983, 39, 3059–3065. (i) Mikolajczyk, M.; Balczewski, P. Synthesis 1984, 691–694. (j) Cameron, A. G.; Hewson, A. T.; Osammor, M. Tetrahedron Lett. 1984, 2267–2270. (k) Takahashi, Y.; Isobe, K.; Hagiwara, H.; Kosugi, H.; Uda, H., J. Chem. Soc., Chem. Commun. 1981, 714–715. (1) Boschelli, D.; Scarborough, R. M., Jr.; Smith, A. B., III. Tetrahedron Lett. 1981, 19–22. (m) Tius, M. A.; Astrab, D. P.; Fauq, A. H.; Ousset, J. B. ; Trehan, S. J. Am. Chem. Soc. 1986, 108, 3438–3442. (n) Reference 9c. d, and f. Pentenomycin: (a) Verlaak, J. M. J.; Klunder, A. J. H.; Zwanenburg, B. Tetrahedron Lett. 1982, 5436–5466. Klunder, A. J. H.; Houwen-Claasen, A. A. M.; Kooy, M. G.; Zwanenburg, B. Tetrahedron Lett. 1987, 1329–1332. Xanthocidin: Smith. A. B., III.; Boschelli, D. J. Org. Chem. 1983, 48, 1217–1226. Sarkomycin: (a) Toki, K. Bull. Chem. Soc. Jpn. 1957, 30, 450. Shemyakin, M. M.; Ravdel, G. A.; Chaman, Ye. S.; Shevtsov, Y. B.; Vinogradova, Ye. I. Chem. Ind. 1957, 1320. Boeckmann, R., Jr.; Naegely, P. C.; Arthur, S. D. J. Org. Chem. 1980, 45, 752. Kobayashi, Y.; Tsuji, J. Tetrahedron Lett. 1981, 4295. (e) Barreiro, E. J. Tetrahedron Lett. 1982, 3605. (f) Wexler, B. A.; Toder, B. H.; Minaskanian, G.; Smith, A. B., III. J. Org. Chem. 1982, 23, 3333. (g) Marx, J. N.; Minaskanian, G. J. J. Org. Chem. 1982, 47, 3306. (h) Hewson, A. T.; McPherson, D. T. Tetrahedron Lett. 1983, 647. (i) Govindan, S. V.; Hudlicky, T.; Koszyk, F. J. Org. Chem. 1983, 28, 3581. (j) Kodpinid, M. M.; Siwapinyoyos, T.; Thebtaranonth, Y. J. Am. Chem. Soc. 1984, 106, 4862. Clavulones: (a) Corey, E. J.; Mehrotra, M. M. J. Am. Chem. Soc. 1984, 106, 3384. Shibasaki, M.; Ogawa, Y. Tetrahedron Lett. 1985, 3841–3844. Hashimoto, S.; Arai, Y.; Hamanaka, H. Tetrahedron Lett. 1985, 2679–2682. Nagaoka, H.; Miyakoshi, T.; Kasuga, J. I. ; Yamada, Y. Tetrahedron Lett. 1985, 5053–5056. Chlorovulones: Nagaoka, H.; Iguchi, K.; Miyakoshi, T.; Yamada, N.; Yamada, Y. Tetrahedron Lett. 1986, 223–226 (1986). Puna-glandins: (a) Nagaoka, H.; Miyaoka, H.; Miyakoshi, Y.; Yamada, Y. J. Am. Chem. Soc. 1986,108, 5019–5021. Suzuki, M.; Morita, Y.; Yanagisawa, A.; Noyori, R.; Baker, B. J., Jr.; Scheuer, P. J. J. Am. Chem. Soc. 1986, 108, 5021–5022. Sasai, H.; Shibasaki, M. Tetrahedron Lett. 1987, 333–337.
    • (1977) Synth. Commun. , vol.7 , pp. 185-188
    • Katsin, N.1    Ikan, R.2
  • 9
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    • Improved procedures will be described shortly.
    • South M. S.; Liebeskind, L. S. J. Org. Chem. 1982, 47, 3815–3821. Improved procedures will be described shortly.
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    • South, M.S.1    Liebeskind, L.S.2
  • 10
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    • Decker, O. H. W.; Moore, H. W. J. Org. Chem. 1987, 52, 1174–1175. Karlsson, K. J. O.; Nguyen, N. V.; Foland, L. D.; Moore, H. W. J. Am. Chem. Soc. 1985, 107, 3392.
    • For some previous examples of this reaction, see: (a) Perri, S. T.; Foland, L. D.; Decker, O. H. W.; Moore, H. W. J. Org. Chem. 1986, 51, 3067–3068. Decker, O. H. W.; Moore, H. W. J. Org. Chem. 1987, 52, 1174–1175. Karlsson, K. J. O.; Nguyen, N. V.; Foland, L. D.; Moore, H. W. J. Am. Chem. Soc. 1985, 107, 3392.
    • (1986) J. Org. Chem. , vol.51 , pp. 3067-3068
    • Perri, S.T.1    Foland, L.D.2    Decker, O.H.W.3    Moore, H.W.4
  • 15
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    • Matz, J. R.; Cohen, T. Tetrahedron Lett. 1981, 2459–2462. Miller J. A Ullah G. M. J. Chem. Soc., Chem. Commun. 1982, 874–875 Jackson, A.; Rey, M.; Dreiding, A. S. Tetrahedron Lett. 1983, 4817–4820. (e) Schmit, C.; Sahraoui-Taleb, S.; Differding, E.; Dehasse-De Lombaert, C. G.; Ghosez, L. Tetrahedron Lett. 1984, 5043–5046. (f) Barnier, J. P. ; Karkour, B.; Salaiin, J. J. Chem. Soc., Chem. Commun. 1985, 1270–1272. (g) Cohen, T.; Yu, L. C. ; Daniewski, W. M. J. Org. Chem. 1985, 50, 4596–4600. (h) Greene, A. E.; Depres, J. P. J. Am, Chem. Soc. 1979, 101, 4003–4005. (i) Depres, J. P. ; Greene, A. E. J. Org. Chem. 1980, 45, 2036–5037. (j) Hamer, N. K. Tetrahedron Lett. 1986, 2167–2168. (k) Krief, A.; Laboureur. J. L. J. Chem. Soc., Chem. Commun. 1986, 702–704. (1) Krief, A.; Laboureur, J. L. Tetrahedron Lett. 1987, 1545–1548. (m) Krief, A.; Laboureur, J. L.; Dumont, W. Tetrahedron Lett. 1987, 1549-1552
    • Gutsche, C. D.; Redmore, D. Carbocyclic Ring Expansion Reactions; Academic Press: New York, 1968. Matz, J. R.; Cohen, T. Tetrahedron Lett. 1981, 2459–2462. Miller, J. A.; Ullah, G. M. J. Chem. Soc., Chem. Commun. 1982, 874–875. Jackson, D. A.; Rey, M.; Dreiding, A. S. Tetrahedron Lett. 1983, 4817–4820. (e) Schmit, C.; Sahraoui-Taleb, S.; Differding, E.; Dehasse-De Lombaert, C. G.; Ghosez, L. Tetrahedron Lett. 1984, 5043–5046. (f) Barnier, J. P. ; Karkour, B.; Salaiin, J. J. Chem. Soc., Chem. Commun. 1985, 1270–1272. (g) Cohen, T.; Yu, L. C. ; Daniewski, W. M. J. Org. Chem. 1985, 50, 4596–4600. (h) Greene, A. E.; Depres, J. P. J. Am, Chem. Soc. 1979, 101, 4003–4005. (i) Depres, J. P. ; Greene, A. E. J. Org. Chem. 1980, 45, 2036–5037. (j) Hamer, N. K. Tetrahedron Lett. 1986, 2167–2168. (k) Krief, A.; Laboureur. J. L. J. Chem. Soc., Chem. Commun. 1986, 702–704. (1) Krief, A.; Laboureur, J. L. Tetrahedron Lett. 1987, 1545–1548. (m) Krief, A.; Laboureur, J. L.; Dumont, W. Tetrahedron Lett. 1987, 1549-1552.
    • (1968) Carbocyclic Ring Expansion Reactions; Academic Press: New York
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