Synthesis of D- and L-Deoxymannojirimycin via an Asymmetric Aminohydroxylation of Vinylfuran

Organic Letters

Volumn 3, Issue 3, 2001, Pages 401-404

  Haukaas, Michael H ^a   O'Doherty, George A ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 DEOXYNOJIRIMYCIN; 2 VINYLFURAN; 2-VINYLFURAN; ENZYME INHIBITOR; FURAN DERIVATIVE;

ARTICLE; CHEMISTRY; HYDROXYLATION; STEREOISOMERISM; SYNTHESIS;

1-DEOXYNOJIRIMYCIN; ENZYME INHIBITORS; FURANS; HYDROXYLATION; STEREOISOMERISM;

EID: 0035825802     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006907j     Document Type: Article

References (50)

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15. For the first synthesis of DGJ, see: (a) Leontein, K.; Lindberg, B.; Lonngren, J. Acta Chem. Scand. B 1982, 36, 515-518. (b) For more recent syntheses, see: Le Merrer, Y.; Poitout, L.; Depezay, J.-C.; Dosbaa, I.; Geoffroy, S. Foglietti, M.-J. Bioorg. Med. Chem. 1997, 5, 519-533. (c) Liao, L.-X.; Wang, Z.-M.; Zhou, W.-S. Tetrahedron: Asymmetry 1999, 10, 3649-57.
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18. For syntheses of DNJ/DMJ before 1994 and a concise approach to DNJ/DMJ from dicarbonyl sugars, see: (a) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175. (b) For syntheses of DMJ after 1994, see: Asano, K.; Hakogi, T.; Iwama, S.; Katsumura, S. Chem. Commun. 1999, 41-42. (c) Campbell, J. A.; Lee, W. K.; Rapoport, H. J. Org. Chem. 1995, 60, 4602-4616. (d) Cook, G. R.; Beholz, L. G.; Stille, J. R. J. Org. Chem. 1994, 59, 3575-3584. (e) Dondoni A.; Perrone, D. J. Org. Chem. 1995, 60, 47-49. (f) Hudlicky, T.; Rouden, J.; Luna, H.; Allen, S. J. Am. Chem. Soc. 1994, 116, 5099-5107. (g) Johnson, C. R.; Golebiowski, A.; Schoffers, E.; Sundram, H.; Braun, M. P. Synlett 1995, 313-314. (h) Lee, S. G.; Yoon, Y. J.; Shin, S. C.; Lee, B. Y.; Cho, S. D.; Kim, S. K.; Lee, J. H. Heterocycles 1997, 45, 701-706. (i) Lemerrer, Y.; Poitout, L.; Depezay, J. C.; Dosbaa, I.; Geoffroy, S.; Foglietti, M. J. Bioorg. Med. Chem. 1997, 5, 519-533. (j) Liao, L.-X.; Wang, Z.-M.; Zhang, H.-X.; Zhou, W.-S. Tetrahedron: Asymmetry 1999, 10, 3649-3657. (k) Meyers, A. I.; Price, D. A.; Andres, C. J. Synlett 1997, 533. (l) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (m) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (n) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (o) Xu, Y.-M.; Zhou, W.-S. Tetrahedron Lett. 1996, 37, 1461-1462. (p) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (q) Asano, K.; Hakogi, T.; Iwama, S. Katsumura, S. Chem Commun. 1999, 41-42.
19. For syntheses of DNJ/DMJ before 1994 and a concise approach to DNJ/DMJ from dicarbonyl sugars, see: (a) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175. (b) For syntheses of DMJ after 1994, see: Asano, K.; Hakogi, T.; Iwama, S.; Katsumura, S. Chem. Commun. 1999, 41-42. (c) Campbell, J. A.; Lee, W. K.; Rapoport, H. J. Org. Chem. 1995, 60, 4602-4616. (d) Cook, G. R.; Beholz, L. G.; Stille, J. R. J. Org. Chem. 1994, 59, 3575-3584. (e) Dondoni A.; Perrone, D. J. Org. Chem. 1995, 60, 47-49. (f) Hudlicky, T.; Rouden, J.; Luna, H.; Allen, S. J. Am. Chem. Soc. 1994, 116, 5099-5107. (g) Johnson, C. R.; Golebiowski, A.; Schoffers, E.; Sundram, H.; Braun, M. P. Synlett 1995, 313-314. (h) Lee, S. G.; Yoon, Y. J.; Shin, S. C.; Lee, B. Y.; Cho, S. D.; Kim, S. K.; Lee, J. H. Heterocycles 1997, 45, 701-706. (i) Lemerrer, Y.; Poitout, L.; Depezay, J. C.; Dosbaa, I.; Geoffroy, S.; Foglietti, M. J. Bioorg. Med. Chem. 1997, 5, 519-533. (j) Liao, L.-X.; Wang, Z.-M.; Zhang, H.-X.; Zhou, W.-S. Tetrahedron: Asymmetry 1999, 10, 3649-3657. (k) Meyers, A. I.; Price, D. A.; Andres, C. J. Synlett 1997, 533. (l) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (m) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (n) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (o) Xu, Y.-M.; Zhou, W.-S. Tetrahedron Lett. 1996, 37, 1461-1462. (p) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (q) Asano, K.; Hakogi, T.; Iwama, S. Katsumura, S. Chem Commun. 1999, 41-42.
20. For syntheses of DNJ/DMJ before 1994 and a concise approach to DNJ/DMJ from dicarbonyl sugars, see: (a) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175. (b) For syntheses of DMJ after 1994, see: Asano, K.; Hakogi, T.; Iwama, S.; Katsumura, S. Chem. Commun. 1999, 41-42. (c) Campbell, J. A.; Lee, W. K.; Rapoport, H. J. Org. Chem. 1995, 60, 4602-4616. (d) Cook, G. R.; Beholz, L. G.; Stille, J. R. J. Org. Chem. 1994, 59, 3575-3584. (e) Dondoni A.; Perrone, D. J. Org. Chem. 1995, 60, 47-49. (f) Hudlicky, T.; Rouden, J.; Luna, H.; Allen, S. J. Am. Chem. Soc. 1994, 116, 5099-5107. (g) Johnson, C. R.; Golebiowski, A.; Schoffers, E.; Sundram, H.; Braun, M. P. Synlett 1995, 313-314. (h) Lee, S. G.; Yoon, Y. J.; Shin, S. C.; Lee, B. Y.; Cho, S. D.; Kim, S. K.; Lee, J. H. Heterocycles 1997, 45, 701-706. (i) Lemerrer, Y.; Poitout, L.; Depezay, J. C.; Dosbaa, I.; Geoffroy, S.; Foglietti, M. J. Bioorg. Med. Chem. 1997, 5, 519-533. (j) Liao, L.-X.; Wang, Z.-M.; Zhang, H.-X.; Zhou, W.-S. Tetrahedron: Asymmetry 1999, 10, 3649-3657. (k) Meyers, A. I.; Price, D. A.; Andres, C. J. Synlett 1997, 533. (l) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (m) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (n) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (o) Xu, Y.-M.; Zhou, W.-S. Tetrahedron Lett. 1996, 37, 1461-1462. (p) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (q) Asano, K.; Hakogi, T.; Iwama, S. Katsumura, S. Chem Commun. 1999, 41-42.
21. For syntheses of DNJ/DMJ before 1994 and a concise approach to DNJ/DMJ from dicarbonyl sugars, see: (a) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175. (b) For syntheses of DMJ after 1994, see: Asano, K.; Hakogi, T.; Iwama, S.; Katsumura, S. Chem. Commun. 1999, 41-42. (c) Campbell, J. A.; Lee, W. K.; Rapoport, H. J. Org. Chem. 1995, 60, 4602-4616. (d) Cook, G. R.; Beholz, L. G.; Stille, J. R. J. Org. Chem. 1994, 59, 3575-3584. (e) Dondoni A.; Perrone, D. J. Org. Chem. 1995, 60, 47-49. (f) Hudlicky, T.; Rouden, J.; Luna, H.; Allen, S. J. Am. Chem. Soc. 1994, 116, 5099-5107. (g) Johnson, C. R.; Golebiowski, A.; Schoffers, E.; Sundram, H.; Braun, M. P. Synlett 1995, 313-314. (h) Lee, S. G.; Yoon, Y. J.; Shin, S. C.; Lee, B. Y.; Cho, S. D.; Kim, S. K.; Lee, J. H. Heterocycles 1997, 45, 701-706. (i) Lemerrer, Y.; Poitout, L.; Depezay, J. C.; Dosbaa, I.; Geoffroy, S.; Foglietti, M. J. Bioorg. Med. Chem. 1997, 5, 519-533. (j) Liao, L.-X.; Wang, Z.-M.; Zhang, H.-X.; Zhou, W.-S. Tetrahedron: Asymmetry 1999, 10, 3649-3657. (k) Meyers, A. I.; Price, D. A.; Andres, C. J. Synlett 1997, 533. (l) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (m) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (n) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (o) Xu, Y.-M.; Zhou, W.-S. Tetrahedron Lett. 1996, 37, 1461-1462. (p) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (q) Asano, K.; Hakogi, T.; Iwama, S. Katsumura, S. Chem Commun. 1999, 41-42.
22. For syntheses of DNJ/DMJ before 1994 and a concise approach to DNJ/DMJ from dicarbonyl sugars, see: (a) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175. (b) For syntheses of DMJ after 1994, see: Asano, K.; Hakogi, T.; Iwama, S.; Katsumura, S. Chem. Commun. 1999, 41-42. (c) Campbell, J. A.; Lee, W. K.; Rapoport, H. J. Org. Chem. 1995, 60, 4602-4616. (d) Cook, G. R.; Beholz, L. G.; Stille, J. R. J. Org. Chem. 1994, 59, 3575-3584. (e) Dondoni A.; Perrone, D. J. Org. Chem. 1995, 60, 47-49. (f) Hudlicky, T.; Rouden, J.; Luna, H.; Allen, S. J. Am. Chem. Soc. 1994, 116, 5099-5107. (g) Johnson, C. R.; Golebiowski, A.; Schoffers, E.; Sundram, H.; Braun, M. P. Synlett 1995, 313-314. (h) Lee, S. G.; Yoon, Y. J.; Shin, S. C.; Lee, B. Y.; Cho, S. D.; Kim, S. K.; Lee, J. H. Heterocycles 1997, 45, 701-706. (i) Lemerrer, Y.; Poitout, L.; Depezay, J. C.; Dosbaa, I.; Geoffroy, S.; Foglietti, M. J. Bioorg. Med. Chem. 1997, 5, 519-533. (j) Liao, L.-X.; Wang, Z.-M.; Zhang, H.-X.; Zhou, W.-S. Tetrahedron: Asymmetry 1999, 10, 3649-3657. (k) Meyers, A. I.; Price, D. A.; Andres, C. J. Synlett 1997, 533. (l) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (m) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (n) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (o) Xu, Y.-M.; Zhou, W.-S. Tetrahedron Lett. 1996, 37, 1461-1462. (p) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (q) Asano, K.; Hakogi, T.; Iwama, S. Katsumura, S. Chem Commun. 1999, 41-42.
23. For syntheses of DNJ/DMJ before 1994 and a concise approach to DNJ/DMJ from dicarbonyl sugars, see: (a) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175. (b) For syntheses of DMJ after 1994, see: Asano, K.; Hakogi, T.; Iwama, S.; Katsumura, S. Chem. Commun. 1999, 41-42. (c) Campbell, J. A.; Lee, W. K.; Rapoport, H. J. Org. Chem. 1995, 60, 4602-4616. (d) Cook, G. R.; Beholz, L. G.; Stille, J. R. J. Org. Chem. 1994, 59, 3575-3584. (e) Dondoni A.; Perrone, D. J. Org. Chem. 1995, 60, 47-49. (f) Hudlicky, T.; Rouden, J.; Luna, H.; Allen, S. J. Am. Chem. Soc. 1994, 116, 5099-5107. (g) Johnson, C. R.; Golebiowski, A.; Schoffers, E.; Sundram, H.; Braun, M. P. Synlett 1995, 313-314. (h) Lee, S. G.; Yoon, Y. J.; Shin, S. C.; Lee, B. Y.; Cho, S. D.; Kim, S. K.; Lee, J. H. Heterocycles 1997, 45, 701-706. (i) Lemerrer, Y.; Poitout, L.; Depezay, J. C.; Dosbaa, I.; Geoffroy, S.; Foglietti, M. J. Bioorg. Med. Chem. 1997, 5, 519-533. (j) Liao, L.-X.; Wang, Z.-M.; Zhang, H.-X.; Zhou, W.-S. Tetrahedron: Asymmetry 1999, 10, 3649-3657. (k) Meyers, A. I.; Price, D. A.; Andres, C. J. Synlett 1997, 533. (l) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (m) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (n) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (o) Xu, Y.-M.; Zhou, W.-S. Tetrahedron Lett. 1996, 37, 1461-1462. (p) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (q) Asano, K.; Hakogi, T.; Iwama, S. Katsumura, S. Chem Commun. 1999, 41-42.
24. For syntheses of DNJ/DMJ before 1994 and a concise approach to DNJ/DMJ from dicarbonyl sugars, see: (a) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175. (b) For syntheses of DMJ after 1994, see: Asano, K.; Hakogi, T.; Iwama, S.; Katsumura, S. Chem. Commun. 1999, 41-42. (c) Campbell, J. A.; Lee, W. K.; Rapoport, H. J. Org. Chem. 1995, 60, 4602-4616. (d) Cook, G. R.; Beholz, L. G.; Stille, J. R. J. Org. Chem. 1994, 59, 3575-3584. (e) Dondoni A.; Perrone, D. J. Org. Chem. 1995, 60, 47-49. (f) Hudlicky, T.; Rouden, J.; Luna, H.; Allen, S. J. Am. Chem. Soc. 1994, 116, 5099-5107. (g) Johnson, C. R.; Golebiowski, A.; Schoffers, E.; Sundram, H.; Braun, M. P. Synlett 1995, 313-314. (h) Lee, S. G.; Yoon, Y. J.; Shin, S. C.; Lee, B. Y.; Cho, S. D.; Kim, S. K.; Lee, J. H. Heterocycles 1997, 45, 701-706. (i) Lemerrer, Y.; Poitout, L.; Depezay, J. C.; Dosbaa, I.; Geoffroy, S.; Foglietti, M. J. Bioorg. Med. Chem. 1997, 5, 519-533. (j) Liao, L.-X.; Wang, Z.-M.; Zhang, H.-X.; Zhou, W.-S. Tetrahedron: Asymmetry 1999, 10, 3649-3657. (k) Meyers, A. I.; Price, D. A.; Andres, C. J. Synlett 1997, 533. (l) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (m) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (n) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (o) Xu, Y.-M.; Zhou, W.-S. Tetrahedron Lett. 1996, 37, 1461-1462. (p) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (q) Asano, K.; Hakogi, T.; Iwama, S. Katsumura, S. Chem Commun. 1999, 41-42.
25. For syntheses of DNJ/DMJ before 1994 and a concise approach to DNJ/DMJ from dicarbonyl sugars, see: (a) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175. (b) For syntheses of DMJ after 1994, see: Asano, K.; Hakogi, T.; Iwama, S.; Katsumura, S. Chem. Commun. 1999, 41-42. (c) Campbell, J. A.; Lee, W. K.; Rapoport, H. J. Org. Chem. 1995, 60, 4602-4616. (d) Cook, G. R.; Beholz, L. G.; Stille, J. R. J. Org. Chem. 1994, 59, 3575-3584. (e) Dondoni A.; Perrone, D. J. Org. Chem. 1995, 60, 47-49. (f) Hudlicky, T.; Rouden, J.; Luna, H.; Allen, S. J. Am. Chem. Soc. 1994, 116, 5099-5107. (g) Johnson, C. R.; Golebiowski, A.; Schoffers, E.; Sundram, H.; Braun, M. P. Synlett 1995, 313-314. (h) Lee, S. G.; Yoon, Y. J.; Shin, S. C.; Lee, B. Y.; Cho, S. D.; Kim, S. K.; Lee, J. H. Heterocycles 1997, 45, 701-706. (i) Lemerrer, Y.; Poitout, L.; Depezay, J. C.; Dosbaa, I.; Geoffroy, S.; Foglietti, M. J. Bioorg. Med. Chem. 1997, 5, 519-533. (j) Liao, L.-X.; Wang, Z.-M.; Zhang, H.-X.; Zhou, W.-S. Tetrahedron: Asymmetry 1999, 10, 3649-3657. (k) Meyers, A. I.; Price, D. A.; Andres, C. J. Synlett 1997, 533. (l) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (m) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (n) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (o) Xu, Y.-M.; Zhou, W.-S. Tetrahedron Lett. 1996, 37, 1461-1462. (p) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (q) Asano, K.; Hakogi, T.; Iwama, S. Katsumura, S. Chem Commun. 1999, 41-42.
26. For syntheses of DNJ/DMJ before 1994 and a concise approach to DNJ/DMJ from dicarbonyl sugars, see: (a) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175. (b) For syntheses of DMJ after 1994, see: Asano, K.; Hakogi, T.; Iwama, S.; Katsumura, S. Chem. Commun. 1999, 41-42. (c) Campbell, J. A.; Lee, W. K.; Rapoport, H. J. Org. Chem. 1995, 60, 4602-4616. (d) Cook, G. R.; Beholz, L. G.; Stille, J. R. J. Org. Chem. 1994, 59, 3575-3584. (e) Dondoni A.; Perrone, D. J. Org. Chem. 1995, 60, 47-49. (f) Hudlicky, T.; Rouden, J.; Luna, H.; Allen, S. J. Am. Chem. Soc. 1994, 116, 5099-5107. (g) Johnson, C. R.; Golebiowski, A.; Schoffers, E.; Sundram, H.; Braun, M. P. Synlett 1995, 313-314. (h) Lee, S. G.; Yoon, Y. J.; Shin, S. C.; Lee, B. Y.; Cho, S. D.; Kim, S. K.; Lee, J. H. Heterocycles 1997, 45, 701-706. (i) Lemerrer, Y.; Poitout, L.; Depezay, J. C.; Dosbaa, I.; Geoffroy, S.; Foglietti, M. J. Bioorg. Med. Chem. 1997, 5, 519-533. (j) Liao, L.-X.; Wang, Z.-M.; Zhang, H.-X.; Zhou, W.-S. Tetrahedron: Asymmetry 1999, 10, 3649-3657. (k) Meyers, A. I.; Price, D. A.; Andres, C. J. Synlett 1997, 533. (l) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (m) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (n) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (o) Xu, Y.-M.; Zhou, W.-S. Tetrahedron Lett. 1996, 37, 1461-1462. (p) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (q) Asano, K.; Hakogi, T.; Iwama, S. Katsumura, S. Chem Commun. 1999, 41-42.
27. For syntheses of DNJ/DMJ before 1994 and a concise approach to DNJ/DMJ from dicarbonyl sugars, see: (a) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175. (b) For syntheses of DMJ after 1994, see: Asano, K.; Hakogi, T.; Iwama, S.; Katsumura, S. Chem. Commun. 1999, 41-42. (c) Campbell, J. A.; Lee, W. K.; Rapoport, H. J. Org. Chem. 1995, 60, 4602-4616. (d) Cook, G. R.; Beholz, L. G.; Stille, J. R. J. Org. Chem. 1994, 59, 3575-3584. (e) Dondoni A.; Perrone, D. J. Org. Chem. 1995, 60, 47-49. (f) Hudlicky, T.; Rouden, J.; Luna, H.; Allen, S. J. Am. Chem. Soc. 1994, 116, 5099-5107. (g) Johnson, C. R.; Golebiowski, A.; Schoffers, E.; Sundram, H.; Braun, M. P. Synlett 1995, 313-314. (h) Lee, S. G.; Yoon, Y. J.; Shin, S. C.; Lee, B. Y.; Cho, S. D.; Kim, S. K.; Lee, J. H. Heterocycles 1997, 45, 701-706. (i) Lemerrer, Y.; Poitout, L.; Depezay, J. C.; Dosbaa, I.; Geoffroy, S.; Foglietti, M. J. Bioorg. Med. Chem. 1997, 5, 519-533. (j) Liao, L.-X.; Wang, Z.-M.; Zhang, H.-X.; Zhou, W.-S. Tetrahedron: Asymmetry 1999, 10, 3649-3657. (k) Meyers, A. I.; Price, D. A.; Andres, C. J. Synlett 1997, 533. (l) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (m) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (n) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (o) Xu, Y.-M.; Zhou, W.-S. Tetrahedron Lett. 1996, 37, 1461-1462. (p) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (q) Asano, K.; Hakogi, T.; Iwama, S. Katsumura, S. Chem Commun. 1999, 41-42.
28. For syntheses of DNJ/DMJ before 1994 and a concise approach to DNJ/DMJ from dicarbonyl sugars, see: (a) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175. (b) For syntheses of DMJ after 1994, see: Asano, K.; Hakogi, T.; Iwama, S.; Katsumura, S. Chem. Commun. 1999, 41-42. (c) Campbell, J. A.; Lee, W. K.; Rapoport, H. J. Org. Chem. 1995, 60, 4602-4616. (d) Cook, G. R.; Beholz, L. G.; Stille, J. R. J. Org. Chem. 1994, 59, 3575-3584. (e) Dondoni A.; Perrone, D. J. Org. Chem. 1995, 60, 47-49. (f) Hudlicky, T.; Rouden, J.; Luna, H.; Allen, S. J. Am. Chem. Soc. 1994, 116, 5099-5107. (g) Johnson, C. R.; Golebiowski, A.; Schoffers, E.; Sundram, H.; Braun, M. P. Synlett 1995, 313-314. (h) Lee, S. G.; Yoon, Y. J.; Shin, S. C.; Lee, B. Y.; Cho, S. D.; Kim, S. K.; Lee, J. H. Heterocycles 1997, 45, 701-706. (i) Lemerrer, Y.; Poitout, L.; Depezay, J. C.; Dosbaa, I.; Geoffroy, S.; Foglietti, M. J. Bioorg. Med. Chem. 1997, 5, 519-533. (j) Liao, L.-X.; Wang, Z.-M.; Zhang, H.-X.; Zhou, W.-S. Tetrahedron: Asymmetry 1999, 10, 3649-3657. (k) Meyers, A. I.; Price, D. A.; Andres, C. J. Synlett 1997, 533. (l) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (m) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (n) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (o) Xu, Y.-M.; Zhou, W.-S. Tetrahedron Lett. 1996, 37, 1461-1462. (p) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (q) Asano, K.; Hakogi, T.; Iwama, S. Katsumura, S. Chem Commun. 1999, 41-42.
29. For syntheses of DNJ/DMJ before 1994 and a concise approach to DNJ/DMJ from dicarbonyl sugars, see: (a) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175. (b) For syntheses of DMJ after 1994, see: Asano, K.; Hakogi, T.; Iwama, S.; Katsumura, S. Chem. Commun. 1999, 41-42. (c) Campbell, J. A.; Lee, W. K.; Rapoport, H. J. Org. Chem. 1995, 60, 4602-4616. (d) Cook, G. R.; Beholz, L. G.; Stille, J. R. J. Org. Chem. 1994, 59, 3575-3584. (e) Dondoni A.; Perrone, D. J. Org. Chem. 1995, 60, 47-49. (f) Hudlicky, T.; Rouden, J.; Luna, H.; Allen, S. J. Am. Chem. Soc. 1994, 116, 5099-5107. (g) Johnson, C. R.; Golebiowski, A.; Schoffers, E.; Sundram, H.; Braun, M. P. Synlett 1995, 313-314. (h) Lee, S. G.; Yoon, Y. J.; Shin, S. C.; Lee, B. Y.; Cho, S. D.; Kim, S. K.; Lee, J. H. Heterocycles 1997, 45, 701-706. (i) Lemerrer, Y.; Poitout, L.; Depezay, J. C.; Dosbaa, I.; Geoffroy, S.; Foglietti, M. J. Bioorg. Med. Chem. 1997, 5, 519-533. (j) Liao, L.-X.; Wang, Z.-M.; Zhang, H.-X.; Zhou, W.-S. Tetrahedron: Asymmetry 1999, 10, 3649-3657. (k) Meyers, A. I.; Price, D. A.; Andres, C. J. Synlett 1997, 533. (l) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (m) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (n) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (o) Xu, Y.-M.; Zhou, W.-S. Tetrahedron Lett. 1996, 37, 1461-1462. (p) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (q) Asano, K.; Hakogi, T.; Iwama, S. Katsumura, S. Chem Commun. 1999, 41-42.
30. For syntheses of DNJ/DMJ before 1994 and a concise approach to DNJ/DMJ from dicarbonyl sugars, see: (a) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175. (b) For syntheses of DMJ after 1994, see: Asano, K.; Hakogi, T.; Iwama, S.; Katsumura, S. Chem. Commun. 1999, 41-42. (c) Campbell, J. A.; Lee, W. K.; Rapoport, H. J. Org. Chem. 1995, 60, 4602-4616. (d) Cook, G. R.; Beholz, L. G.; Stille, J. R. J. Org. Chem. 1994, 59, 3575-3584. (e) Dondoni A.; Perrone, D. J. Org. Chem. 1995, 60, 47-49. (f) Hudlicky, T.; Rouden, J.; Luna, H.; Allen, S. J. Am. Chem. Soc. 1994, 116, 5099-5107. (g) Johnson, C. R.; Golebiowski, A.; Schoffers, E.; Sundram, H.; Braun, M. P. Synlett 1995, 313-314. (h) Lee, S. G.; Yoon, Y. J.; Shin, S. C.; Lee, B. Y.; Cho, S. D.; Kim, S. K.; Lee, J. H. Heterocycles 1997, 45, 701-706. (i) Lemerrer, Y.; Poitout, L.; Depezay, J. C.; Dosbaa, I.; Geoffroy, S.; Foglietti, M. J. Bioorg. Med. Chem. 1997, 5, 519-533. (j) Liao, L.-X.; Wang, Z.-M.; Zhang, H.-X.; Zhou, W.-S. Tetrahedron: Asymmetry 1999, 10, 3649-3657. (k) Meyers, A. I.; Price, D. A.; Andres, C. J. Synlett 1997, 533. (l) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (m) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (n) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (o) Xu, Y.-M.; Zhou, W.-S. Tetrahedron Lett. 1996, 37, 1461-1462. (p) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (q) Asano, K.; Hakogi, T.; Iwama, S. Katsumura, S. Chem Commun. 1999, 41-42.
31. For syntheses of DNJ/DMJ before 1994 and a concise approach to DNJ/DMJ from dicarbonyl sugars, see: (a) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175. (b) For syntheses of DMJ after 1994, see: Asano, K.; Hakogi, T.; Iwama, S.; Katsumura, S. Chem. Commun. 1999, 41-42. (c) Campbell, J. A.; Lee, W. K.; Rapoport, H. J. Org. Chem. 1995, 60, 4602-4616. (d) Cook, G. R.; Beholz, L. G.; Stille, J. R. J. Org. Chem. 1994, 59, 3575-3584. (e) Dondoni A.; Perrone, D. J. Org. Chem. 1995, 60, 47-49. (f) Hudlicky, T.; Rouden, J.; Luna, H.; Allen, S. J. Am. Chem. Soc. 1994, 116, 5099-5107. (g) Johnson, C. R.; Golebiowski, A.; Schoffers, E.; Sundram, H.; Braun, M. P. Synlett 1995, 313-314. (h) Lee, S. G.; Yoon, Y. J.; Shin, S. C.; Lee, B. Y.; Cho, S. D.; Kim, S. K.; Lee, J. H. Heterocycles 1997, 45, 701-706. (i) Lemerrer, Y.; Poitout, L.; Depezay, J. C.; Dosbaa, I.; Geoffroy, S.; Foglietti, M. J. Bioorg. Med. Chem. 1997, 5, 519-533. (j) Liao, L.-X.; Wang, Z.-M.; Zhang, H.-X.; Zhou, W.-S. Tetrahedron: Asymmetry 1999, 10, 3649-3657. (k) Meyers, A. I.; Price, D. A.; Andres, C. J. Synlett 1997, 533. (l) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (m) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (n) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (o) Xu, Y.-M.; Zhou, W.-S. Tetrahedron Lett. 1996, 37, 1461-1462. (p) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (q) Asano, K.; Hakogi, T.; Iwama, S. Katsumura, S. Chem Commun. 1999, 41-42.
32. For syntheses of DNJ/DMJ before 1994 and a concise approach to DNJ/DMJ from dicarbonyl sugars, see: (a) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175. (b) For syntheses of DMJ after 1994, see: Asano, K.; Hakogi, T.; Iwama, S.; Katsumura, S. Chem. Commun. 1999, 41-42. (c) Campbell, J. A.; Lee, W. K.; Rapoport, H. J. Org. Chem. 1995, 60, 4602-4616. (d) Cook, G. R.; Beholz, L. G.; Stille, J. R. J. Org. Chem. 1994, 59, 3575-3584. (e) Dondoni A.; Perrone, D. J. Org. Chem. 1995, 60, 47-49. (f) Hudlicky, T.; Rouden, J.; Luna, H.; Allen, S. J. Am. Chem. Soc. 1994, 116, 5099-5107. (g) Johnson, C. R.; Golebiowski, A.; Schoffers, E.; Sundram, H.; Braun, M. P. Synlett 1995, 313-314. (h) Lee, S. G.; Yoon, Y. J.; Shin, S. C.; Lee, B. Y.; Cho, S. D.; Kim, S. K.; Lee, J. H. Heterocycles 1997, 45, 701-706. (i) Lemerrer, Y.; Poitout, L.; Depezay, J. C.; Dosbaa, I.; Geoffroy, S.; Foglietti, M. J. Bioorg. Med. Chem. 1997, 5, 519-533. (j) Liao, L.-X.; Wang, Z.-M.; Zhang, H.-X.; Zhou, W.-S. Tetrahedron: Asymmetry 1999, 10, 3649-3657. (k) Meyers, A. I.; Price, D. A.; Andres, C. J. Synlett 1997, 533. (l) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (m) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (n) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (o) Xu, Y.-M.; Zhou, W.-S. Tetrahedron Lett. 1996, 37, 1461-1462. (p) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (q) Asano, K.; Hakogi, T.; Iwama, S. Katsumura, S. Chem Commun. 1999, 41-42.
33. For syntheses of DNJ/DMJ before 1994 and a concise approach to DNJ/DMJ from dicarbonyl sugars, see: (a) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175. (b) For syntheses of DMJ after 1994, see: Asano, K.; Hakogi, T.; Iwama, S.; Katsumura, S. Chem. Commun. 1999, 41-42. (c) Campbell, J. A.; Lee, W. K.; Rapoport, H. J. Org. Chem. 1995, 60, 4602-4616. (d) Cook, G. R.; Beholz, L. G.; Stille, J. R. J. Org. Chem. 1994, 59, 3575-3584. (e) Dondoni A.; Perrone, D. J. Org. Chem. 1995, 60, 47-49. (f) Hudlicky, T.; Rouden, J.; Luna, H.; Allen, S. J. Am. Chem. Soc. 1994, 116, 5099-5107. (g) Johnson, C. R.; Golebiowski, A.; Schoffers, E.; Sundram, H.; Braun, M. P. Synlett 1995, 313-314. (h) Lee, S. G.; Yoon, Y. J.; Shin, S. C.; Lee, B. Y.; Cho, S. D.; Kim, S. K.; Lee, J. H. Heterocycles 1997, 45, 701-706. (i) Lemerrer, Y.; Poitout, L.; Depezay, J. C.; Dosbaa, I.; Geoffroy, S.; Foglietti, M. J. Bioorg. Med. Chem. 1997, 5, 519-533. (j) Liao, L.-X.; Wang, Z.-M.; Zhang, H.-X.; Zhou, W.-S. Tetrahedron: Asymmetry 1999, 10, 3649-3657. (k) Meyers, A. I.; Price, D. A.; Andres, C. J. Synlett 1997, 533. (l) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (m) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (n) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (o) Xu, Y.-M.; Zhou, W.-S. Tetrahedron Lett. 1996, 37, 1461-1462. (p) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (q) Asano, K.; Hakogi, T.; Iwama, S. Katsumura, S. Chem Commun. 1999, 41-42.
34. For syntheses of DNJ/DMJ before 1994 and a concise approach to DNJ/DMJ from dicarbonyl sugars, see: (a) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175. (b) For syntheses of DMJ after 1994, see: Asano, K.; Hakogi, T.; Iwama, S.; Katsumura, S. Chem. Commun. 1999, 41-42. (c) Campbell, J. A.; Lee, W. K.; Rapoport, H. J. Org. Chem. 1995, 60, 4602-4616. (d) Cook, G. R.; Beholz, L. G.; Stille, J. R. J. Org. Chem. 1994, 59, 3575-3584. (e) Dondoni A.; Perrone, D. J. Org. Chem. 1995, 60, 47-49. (f) Hudlicky, T.; Rouden, J.; Luna, H.; Allen, S. J. Am. Chem. Soc. 1994, 116, 5099-5107. (g) Johnson, C. R.; Golebiowski, A.; Schoffers, E.; Sundram, H.; Braun, M. P. Synlett 1995, 313-314. (h) Lee, S. G.; Yoon, Y. J.; Shin, S. C.; Lee, B. Y.; Cho, S. D.; Kim, S. K.; Lee, J. H. Heterocycles 1997, 45, 701-706. (i) Lemerrer, Y.; Poitout, L.; Depezay, J. C.; Dosbaa, I.; Geoffroy, S.; Foglietti, M. J. Bioorg. Med. Chem. 1997, 5, 519-533. (j) Liao, L.-X.; Wang, Z.-M.; Zhang, H.-X.; Zhou, W.-S. Tetrahedron: Asymmetry 1999, 10, 3649-3657. (k) Meyers, A. I.; Price, D. A.; Andres, C. J. Synlett 1997, 533. (l) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (m) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (n) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (o) Xu, Y.-M.; Zhou, W.-S. Tetrahedron Lett. 1996, 37, 1461-1462. (p) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (q) Asano, K.; Hakogi, T.; Iwama, S. Katsumura, S. Chem Commun. 1999, 41-42.
35. For an excellent review of the subject, see: Ciufolini, M. A.; Hermann, C. Y. W.; Dong, Q.; Shimizu, T.; Swaminathan, S.; Xi, N. Synlett 1998, 105.
36. Previously, Ciufolini/Wong and Zhou have shown that furans similar to 5 can be produced via resolution strategies: (a) Drueckhammer, D. G.; Barbas, C. F., III; Nozaki, K.; Wong, C.-H.; Wood, C. Y.; Ciufolini, M. A. J. Org. Chem. 1988, 53, 1607. (b) Xu, Y.-M.; Zhou, W.-S. Tetrahedron Lett. 1996, 37, 1461.
37. Previously, Ciufolini/Wong and Zhou have shown that furans similar to 5 can be produced via resolution strategies: (a) Drueckhammer, D. G.; Barbas, C. F., III; Nozaki, K.; Wong, C.-H.; Wood, C. Y.; Ciufolini, M. A. J. Org. Chem. 1988, 53, 1607. (b) Xu, Y.-M.; Zhou, W.-S. Tetrahedron Lett. 1996, 37, 1461.
38. (a) Xi, N.; Ciufolini, M. A. Tetrahedron Lett. 1995, 36, 6595.
39. (b) Yang, C.-F.; Xu, Y.-M.; Liao, L.-X.; Zhou, W.-S. Tetrahedron Lett. 1998, 39, 9227.
40. Altenbach, H.-J.; Wischnat, R. Tetrahedron Lett. 1995, 36, 4983.
41. Li, G. G.; Angert, H. H.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2813-2817.
42. Bushey, M. L.; Haukaas, M. H.; O'Doherty, G. A. J. Org. Chem. 1999, 64, 2984.
43. Harris, J. M.; Keranen, M. D.; O'Doherty, G. A., J. Org. Chem. 1999, 64, 2982.
44. This constitutes an improved procedure as to our previously published procedure (ref 16).
45. At a smaller scale, the level of enantioinduction has been as high as 94%, as determined by Mosher ester analysis. (a) Sullivan, G. R.; Dale, J. A.; Mosher, H. S. J. Org. Chem. 1973, 38, 2143. (b) Yamaguchi, S.; Yasuhara, F.; Kabuto, K. T. Tetrahedron 1976, 32, 1363.
46. At a smaller scale, the level of enantioinduction has been as high as 94%, as determined by Mosher ester analysis. (a) Sullivan, G. R.; Dale, J. A.; Mosher, H. S. J. Org. Chem. 1973, 38, 2143. (b) Yamaguchi, S.; Yasuhara, F.; Kabuto, K. T. Tetrahedron 1976, 32, 1363.
47. Luche, J.-L. J. Am. Chem. Soc. 1978, 110, 2226.
48. Mocerino, M.; Stick, R. V. Aust. J. Chem. 1990, 43, 1183-1193.
49. 1H NMR as doublets with coupling constant of <2 Hz.
50. Hardick, D. J.; Hutchinson, D. W.; Trew, S. J.; Wellington, E. M. H. Tetrahedron 1992, 48, 6285.