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Volumn 63, Issue 15, 1998, Pages 5169-5172

Highly Enantioselective 1,2-Addition of 2-[(Trimethylsilyl)oxy]furan to Aldehydes: Application to Muricatacin Synthesis

Author keywords

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Indexed keywords


EID: 0000379338     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9804137     Document Type: Article
Times cited : (69)

References (38)
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    • With diamines: (a) Kobayashi, S.; Horibe, M. J. Am. Chem. Soc. 1994. 116, 9805-9806. (b) Kobayashi, S.; Hayashi, T. J. Org. Chem. 1995, 60, 1098-1099. (c) Kobayashi, S.; Horibe, M. Tetrahedron 1996, 52, 7277-7286; with Binol derivatives. (d) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649. (e) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. (f) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. (g) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1993, 115, 7039. (h) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4078. (i) Carreira, E. M.; Singer, R. A.; Lee, W. J. Am. Chem. Soc. 1994, 116, 8837. (j) Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649. (k) Singer, R. A.; Carreira, E. M. Tetrahedron Lett. 1997, 38, 927.
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    • Mikami, K.1    Matsukawa, S.2
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    • With diamines: (a) Kobayashi, S.; Horibe, M. J. Am. Chem. Soc. 1994. 116, 9805-9806. (b) Kobayashi, S.; Hayashi, T. J. Org. Chem. 1995, 60, 1098-1099. (c) Kobayashi, S.; Horibe, M. Tetrahedron 1996, 52, 7277-7286; with Binol derivatives. (d) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649. (e) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. (f) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. (g) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1993, 115, 7039. (h) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4078. (i) Carreira, E. M.; Singer, R. A.; Lee, W. J. Am. Chem. Soc. 1994, 116, 8837. (j) Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649. (k) Singer, R. A.; Carreira, E. M. Tetrahedron Lett. 1997, 38, 927.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 4078
    • Mikami, K.1    Matsukawa, S.2
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    • With diamines: (a) Kobayashi, S.; Horibe, M. J. Am. Chem. Soc. 1994. 116, 9805-9806. (b) Kobayashi, S.; Hayashi, T. J. Org. Chem. 1995, 60, 1098-1099. (c) Kobayashi, S.; Horibe, M. Tetrahedron 1996, 52, 7277-7286; with Binol derivatives. (d) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649. (e) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. (f) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. (g) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1993, 115, 7039. (h) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4078. (i) Carreira, E. M.; Singer, R. A.; Lee, W. J. Am. Chem. Soc. 1994, 116, 8837. (j) Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649. (k) Singer, R. A.; Carreira, E. M. Tetrahedron Lett. 1997, 38, 927.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 8837
    • Carreira, E.M.1    Singer, R.A.2    Lee, W.3
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    • 0000778829 scopus 로고
    • With diamines: (a) Kobayashi, S.; Horibe, M. J. Am. Chem. Soc. 1994. 116, 9805-9806. (b) Kobayashi, S.; Hayashi, T. J. Org. Chem. 1995, 60, 1098-1099. (c) Kobayashi, S.; Horibe, M. Tetrahedron 1996, 52, 7277-7286; with Binol derivatives. (d) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649. (e) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. (f) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. (g) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1993, 115, 7039. (h) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4078. (i) Carreira, E. M.; Singer, R. A.; Lee, W. J. Am. Chem. Soc. 1994, 116, 8837. (j) Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649. (k) Singer, R. A.; Carreira, E. M. Tetrahedron Lett. 1997, 38, 927.
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    • Carreira, E.M.1    Lee, W.2    Singer, R.A.3
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    • With diamines: (a) Kobayashi, S.; Horibe, M. J. Am. Chem. Soc. 1994. 116, 9805-9806. (b) Kobayashi, S.; Hayashi, T. J. Org. Chem. 1995, 60, 1098-1099. (c) Kobayashi, S.; Horibe, M. Tetrahedron 1996, 52, 7277-7286; with Binol derivatives. (d) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649. (e) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. (f) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. (g) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1993, 115, 7039. (h) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4078. (i) Carreira, E. M.; Singer, R. A.; Lee, W. J. Am. Chem. Soc. 1994, 116, 8837. (j) Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649. (k) Singer, R. A.; Carreira, E. M. Tetrahedron Lett. 1997, 38, 927.
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    • Recent Advances in the acetogenins of Annonaceae
    • Downum, K. R., Romeo, J. T., Stafford, H. E., Eds.; Plenum Press: New York
    • For recent reviews (on isolation and synthesis) on annonaceous acetogenins, see: (a) Cavé, A.; Cortes, D.; Figadère, B.; Hocquemiller, R.; Laprévote, O.; Laurens, A.; Leboeuf, M. Recent Advances in the acetogenins of Annonaceae. In Photochemical potentiel of Tropical Plants; Downum, K. R., Romeo, J. T., Stafford, H. E., Eds.; Plenum Press: New York, 1993; pp 167-202. (b) Figadère, B. Acc. Chem. Res. 1995, 28, 359-365. (c) Cavé, A.; Figadère, B.; Laurens, A.; Cortes, D. In Progress in the Chemistry of Natural Products; Herz, W., Eds.; Springer-Verlag: Wien, Austria; New York, 1997; Vol. 70, pp 81-288. (d) Figadère, B.; Cavé, A. Studies in Natural Products Chemistry. In Stereoselective Synthesis; Atta-ur-Raman, Ed.; Elsevier: Amsterdam, 1996; Vol. 18, pp 193-227; for the more recent paper on this topic, see: (e) Peyrat, J.-F.; Mahuteau, J.; Figadère, B.; Cavé, A. J. Org. Chem. 1997, 62, 4811-4815.
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    • For recent reviews (on isolation and synthesis) on annonaceous acetogenins, see: (a) Cavé, A.; Cortes, D.; Figadère, B.; Hocquemiller, R.; Laprévote, O.; Laurens, A.; Leboeuf, M. Recent Advances in the acetogenins of Annonaceae. In Photochemical potentiel of Tropical Plants; Downum, K. R., Romeo, J. T., Stafford, H. E., Eds.; Plenum Press: New York, 1993; pp 167-202. (b) Figadère, B. Acc. Chem. Res. 1995, 28, 359-365. (c) Cavé, A.; Figadère, B.; Laurens, A.; Cortes, D. In Progress in the Chemistry of Natural Products; Herz, W., Eds.; Springer-Verlag: Wien, Austria; New York, 1997; Vol. 70, pp 81-288. (d) Figadère, B.; Cavé, A. Studies in Natural Products Chemistry. In Stereoselective Synthesis; Atta-ur-Raman, Ed.; Elsevier: Amsterdam, 1996; Vol. 18, pp 193-227; for the more recent paper on this topic, see: (e) Peyrat, J.-F.; Mahuteau, J.; Figadère, B.; Cavé, A. J. Org. Chem. 1997, 62, 4811-4815.
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    • For recent reviews (on isolation and synthesis) on annonaceous acetogenins, see: (a) Cavé, A.; Cortes, D.; Figadère, B.; Hocquemiller, R.; Laprévote, O.; Laurens, A.; Leboeuf, M. Recent Advances in the acetogenins of Annonaceae. In Photochemical potentiel of Tropical Plants; Downum, K. R., Romeo, J. T., Stafford, H. E., Eds.; Plenum Press: New York, 1993; pp 167-202. (b) Figadère, B. Acc. Chem. Res. 1995, 28, 359-365. (c) Cavé, A.; Figadère, B.; Laurens, A.; Cortes, D. In Progress in the Chemistry of Natural Products; Herz, W., Eds.; Springer-Verlag: Wien, Austria; New York, 1997; Vol. 70, pp 81-288. (d) Figadère, B.; Cavé, A. Studies in Natural Products Chemistry. In Stereoselective Synthesis; Atta-ur-Raman, Ed.; Elsevier: Amsterdam, 1996; Vol. 18, pp 193-227; for the more recent paper on this topic, see: (e) Peyrat, J.-F.; Mahuteau, J.; Figadère, B.; Cavé, A. J. Org. Chem. 1997, 62, 4811-4815.
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    • Studies in Natural Products Chemistry
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    • For recent reviews (on isolation and synthesis) on annonaceous acetogenins, see: (a) Cavé, A.; Cortes, D.; Figadère, B.; Hocquemiller, R.; Laprévote, O.; Laurens, A.; Leboeuf, M. Recent Advances in the acetogenins of Annonaceae. In Photochemical potentiel of Tropical Plants; Downum, K. R., Romeo, J. T., Stafford, H. E., Eds.; Plenum Press: New York, 1993; pp 167-202. (b) Figadère, B. Acc. Chem. Res. 1995, 28, 359-365. (c) Cavé, A.; Figadère, B.; Laurens, A.; Cortes, D. In Progress in the Chemistry of Natural Products; Herz, W., Eds.; Springer-Verlag: Wien, Austria; New York, 1997; Vol. 70, pp 81-288. (d) Figadère, B.; Cavé, A. Studies in Natural Products Chemistry. In Stereoselective Synthesis; Atta-ur-Raman, Ed.; Elsevier: Amsterdam, 1996; Vol. 18, pp 193-227; for the more recent paper on this topic, see: (e) Peyrat, J.-F.; Mahuteau, J.; Figadère, B.; Cavé, A. J. Org. Chem. 1997, 62, 4811-4815.
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    • For recent reviews (on isolation and synthesis) on annonaceous acetogenins, see: (a) Cavé, A.; Cortes, D.; Figadère, B.; Hocquemiller, R.; Laprévote, O.; Laurens, A.; Leboeuf, M. Recent Advances in the acetogenins of Annonaceae. In Photochemical potentiel of Tropical Plants; Downum, K. R., Romeo, J. T., Stafford, H. E., Eds.; Plenum Press: New York, 1993; pp 167-202. (b) Figadère, B. Acc. Chem. Res. 1995, 28, 359-365. (c) Cavé, A.; Figadère, B.; Laurens, A.; Cortes, D. In Progress in the Chemistry of Natural Products; Herz, W., Eds.; Springer-Verlag: Wien, Austria; New York, 1997; Vol. 70, pp 81-288. (d) Figadère, B.; Cavé, A. Studies in Natural Products Chemistry. In Stereoselective Synthesis; Atta-ur-Raman, Ed.; Elsevier: Amsterdam, 1996; Vol. 18, pp 193-227; for the more recent paper on this topic, see: (e) Peyrat, J.-F.; Mahuteau, J.; Figadère, B.; Cavé, A. J. Org. Chem. 1997, 62, 4811-4815.
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    • However, the reaction was run on 1 mmol scale and did not allow us to recrystallize (+)-muricatacin
    • However, the reaction was run on 1 mmol scale and did not allow us to recrystallize (+)-muricatacin.


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