Conversion of D-Glucose to Cyclitol with Hydroxymethyl Substituent via Intramolecular Silyl Nitronate Cycloaddition Reaction: Application to Total Synthesis of (+)-Cyclophellitol

Organic Letters

Volumn 5, Issue 21, 2003, Pages 3879-3882

  Ishikawa, Teruhiko ^b   Shimizu, Yoshihiro ^a   Kudoh, Takayuki ^a   Saito, Seiki ^a  

^a School of Engineering   (Japan)

^b OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 NITRO 6 HEPTENE 2,3,4,5 TETRAOL; ACID; ALCOHOL DERIVATIVE; ALDEHYDE; ALKENE DERIVATIVE; CYCLITOL; CYCLOPHELLITOL; GLUCOSE; METHYL GROUP; NITROMETHANE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLOADDITION; HENRY REACTION; STEREOISOMERISM; SUBSTITUTION REACTION; SYNTHESIS;

EID: 0242460260     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035424n     Document Type: Article

References (32)

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6. For the enantioselective total synthesis of 1, see: (a) Akiyama, T.; Ohnari, M.; Shima, H.; Ozaki, S. Synlett 1991, 831-832. (b) Shing, T. K. M.; Tai, V. W.-F. J. Chem. Soc., Perkin Trans. 1 1994, 2017-2025. (c) McDevitt, R. E.; Fraser-Reid, B. J. Org. Chem. 1994, 59, 3250-3252. (d) Sato, K.; Bokura, M. ; Moriyama, H.; Igarashi, T. Chem. Lett. 1994, 37-40. (e) Jung, M. E.; Choe, S. W. T. J. Org. Chem. 1995, 60, 3280-3281. (f) Schlessinger, R. H.; Bergstrom, C. P. J. Org. Chem. 1995, 60, 16-17. (g) Letellier, P.; Ralainairina, R.; Beaupère, D.; Uzan, R. Synthesis 1997, 925-930. (h) Takahashi, H.; Iimori, T.; Ikegami, S. Tetahedron Lett. 1998, 39, 6939-6942. (i) Ziegler, F. E.; Wang, Y. J. Org. Chem. 1998, 63, 426-427; see also J. Org. Chem. 1998, 63, 7920-7930. (j) Trost, B. M.; Patterson, D. E.; Hembre, E. J. Chem. Eur. J. 2001, 7, 3768-3775.
7. For the enantioselective total synthesis of 1, see: (a) Akiyama, T.; Ohnari, M.; Shima, H.; Ozaki, S. Synlett 1991, 831-832. (b) Shing, T. K. M.; Tai, V. W.-F. J. Chem. Soc., Perkin Trans. 1 1994, 2017-2025. (c) McDevitt, R. E.; Fraser-Reid, B. J. Org. Chem. 1994, 59, 3250-3252. (d) Sato, K.; Bokura, M. ; Moriyama, H.; Igarashi, T. Chem. Lett. 1994, 37-40. (e) Jung, M. E.; Choe, S. W. T. J. Org. Chem. 1995, 60, 3280-3281. (f) Schlessinger, R. H.; Bergstrom, C. P. J. Org. Chem. 1995, 60, 16-17. (g) Letellier, P.; Ralainairina, R.; Beaupère, D.; Uzan, R. Synthesis 1997, 925-930. (h) Takahashi, H.; Iimori, T.; Ikegami, S. Tetahedron Lett. 1998, 39, 6939-6942. (i) Ziegler, F. E.; Wang, Y. J. Org. Chem. 1998, 63, 426-427; see also J. Org. Chem. 1998, 63, 7920-7930. (j) Trost, B. M.; Patterson, D. E.; Hembre, E. J. Chem. Eur. J. 2001, 7, 3768-3775.
8. For the enantioselective total synthesis of 1, see: (a) Akiyama, T.; Ohnari, M.; Shima, H.; Ozaki, S. Synlett 1991, 831-832. (b) Shing, T. K. M.; Tai, V. W.-F. J. Chem. Soc., Perkin Trans. 1 1994, 2017-2025. (c) McDevitt, R. E.; Fraser-Reid, B. J. Org. Chem. 1994, 59, 3250-3252. (d) Sato, K.; Bokura, M. ; Moriyama, H.; Igarashi, T. Chem. Lett. 1994, 37-40. (e) Jung, M. E.; Choe, S. W. T. J. Org. Chem. 1995, 60, 3280-3281. (f) Schlessinger, R. H.; Bergstrom, C. P. J. Org. Chem. 1995, 60, 16-17. (g) Letellier, P.; Ralainairina, R.; Beaupère, D.; Uzan, R. Synthesis 1997, 925-930. (h) Takahashi, H.; Iimori, T.; Ikegami, S. Tetahedron Lett. 1998, 39, 6939-6942. (i) Ziegler, F. E.; Wang, Y. J. Org. Chem. 1998, 63, 426-427; see also J. Org. Chem. 1998, 63, 7920-7930. (j) Trost, B. M.; Patterson, D. E.; Hembre, E. J. Chem. Eur. J. 2001, 7, 3768-3775.
9. For the enantioselective total synthesis of 1, see: (a) Akiyama, T.; Ohnari, M.; Shima, H.; Ozaki, S. Synlett 1991, 831-832. (b) Shing, T. K. M.; Tai, V. W.-F. J. Chem. Soc., Perkin Trans. 1 1994, 2017-2025. (c) McDevitt, R. E.; Fraser-Reid, B. J. Org. Chem. 1994, 59, 3250-3252. (d) Sato, K.; Bokura, M. ; Moriyama, H.; Igarashi, T. Chem. Lett. 1994, 37-40. (e) Jung, M. E.; Choe, S. W. T. J. Org. Chem. 1995, 60, 3280-3281. (f) Schlessinger, R. H.; Bergstrom, C. P. J. Org. Chem. 1995, 60, 16-17. (g) Letellier, P.; Ralainairina, R.; Beaupère, D.; Uzan, R. Synthesis 1997, 925-930. (h) Takahashi, H.; Iimori, T.; Ikegami, S. Tetahedron Lett. 1998, 39, 6939-6942. (i) Ziegler, F. E.; Wang, Y. J. Org. Chem. 1998, 63, 426-427; see also J. Org. Chem. 1998, 63, 7920-7930. (j) Trost, B. M.; Patterson, D. E.; Hembre, E. J. Chem. Eur. J. 2001, 7, 3768-3775.
10. For the enantioselective total synthesis of 1, see: (a) Akiyama, T.; Ohnari, M.; Shima, H.; Ozaki, S. Synlett 1991, 831-832. (b) Shing, T. K. M.; Tai, V. W.-F. J. Chem. Soc., Perkin Trans. 1 1994, 2017-2025. (c) McDevitt, R. E.; Fraser-Reid, B. J. Org. Chem. 1994, 59, 3250-3252. (d) Sato, K.; Bokura, M. ; Moriyama, H.; Igarashi, T. Chem. Lett. 1994, 37-40. (e) Jung, M. E.; Choe, S. W. T. J. Org. Chem. 1995, 60, 3280-3281. (f) Schlessinger, R. H.; Bergstrom, C. P. J. Org. Chem. 1995, 60, 16-17. (g) Letellier, P.; Ralainairina, R.; Beaupère, D.; Uzan, R. Synthesis 1997, 925-930. (h) Takahashi, H.; Iimori, T.; Ikegami, S. Tetahedron Lett. 1998, 39, 6939-6942. (i) Ziegler, F. E.; Wang, Y. J. Org. Chem. 1998, 63, 426-427; see also J. Org. Chem. 1998, 63, 7920-7930. (j) Trost, B. M.; Patterson, D. E.; Hembre, E. J. Chem. Eur. J. 2001, 7, 3768-3775.
11. For the enantioselective total synthesis of 1, see: (a) Akiyama, T.; Ohnari, M.; Shima, H.; Ozaki, S. Synlett 1991, 831-832. (b) Shing, T. K. M.; Tai, V. W.-F. J. Chem. Soc., Perkin Trans. 1 1994, 2017-2025. (c) McDevitt, R. E.; Fraser-Reid, B. J. Org. Chem. 1994, 59, 3250-3252. (d) Sato, K.; Bokura, M. ; Moriyama, H.; Igarashi, T. Chem. Lett. 1994, 37-40. (e) Jung, M. E.; Choe, S. W. T. J. Org. Chem. 1995, 60, 3280-3281. (f) Schlessinger, R. H.; Bergstrom, C. P. J. Org. Chem. 1995, 60, 16-17. (g) Letellier, P.; Ralainairina, R.; Beaupère, D.; Uzan, R. Synthesis 1997, 925-930. (h) Takahashi, H.; Iimori, T.; Ikegami, S. Tetahedron Lett. 1998, 39, 6939-6942. (i) Ziegler, F. E.; Wang, Y. J. Org. Chem. 1998, 63, 426-427; see also J. Org. Chem. 1998, 63, 7920-7930. (j) Trost, B. M.; Patterson, D. E.; Hembre, E. J. Chem. Eur. J. 2001, 7, 3768-3775.
12. For the enantioselective total synthesis of 1, see: (a) Akiyama, T.; Ohnari, M.; Shima, H.; Ozaki, S. Synlett 1991, 831-832. (b) Shing, T. K. M.; Tai, V. W.-F. J. Chem. Soc., Perkin Trans. 1 1994, 2017-2025. (c) McDevitt, R. E.; Fraser-Reid, B. J. Org. Chem. 1994, 59, 3250-3252. (d) Sato, K.; Bokura, M. ; Moriyama, H.; Igarashi, T. Chem. Lett. 1994, 37-40. (e) Jung, M. E.; Choe, S. W. T. J. Org. Chem. 1995, 60, 3280-3281. (f) Schlessinger, R. H.; Bergstrom, C. P. J. Org. Chem. 1995, 60, 16-17. (g) Letellier, P.; Ralainairina, R.; Beaupère, D.; Uzan, R. Synthesis 1997, 925-930. (h) Takahashi, H.; Iimori, T.; Ikegami, S. Tetahedron Lett. 1998, 39, 6939-6942. (i) Ziegler, F. E.; Wang, Y. J. Org. Chem. 1998, 63, 426-427; see also J. Org. Chem. 1998, 63, 7920-7930. (j) Trost, B. M.; Patterson, D. E.; Hembre, E. J. Chem. Eur. J. 2001, 7, 3768-3775.
13. For the enantioselective total synthesis of 1, see: (a) Akiyama, T.; Ohnari, M.; Shima, H.; Ozaki, S. Synlett 1991, 831-832. (b) Shing, T. K. M.; Tai, V. W.-F. J. Chem. Soc., Perkin Trans. 1 1994, 2017-2025. (c) McDevitt, R. E.; Fraser-Reid, B. J. Org. Chem. 1994, 59, 3250-3252. (d) Sato, K.; Bokura, M. ; Moriyama, H.; Igarashi, T. Chem. Lett. 1994, 37-40. (e) Jung, M. E.; Choe, S. W. T. J. Org. Chem. 1995, 60, 3280-3281. (f) Schlessinger, R. H.; Bergstrom, C. P. J. Org. Chem. 1995, 60, 16-17. (g) Letellier, P.; Ralainairina, R.; Beaupère, D.; Uzan, R. Synthesis 1997, 925-930. (h) Takahashi, H.; Iimori, T.; Ikegami, S. Tetahedron Lett. 1998, 39, 6939-6942. (i) Ziegler, F. E.; Wang, Y. J. Org. Chem. 1998, 63, 426-427; see also J. Org. Chem. 1998, 63, 7920-7930. (j) Trost, B. M.; Patterson, D. E.; Hembre, E. J. Chem. Eur. J. 2001, 7, 3768-3775.
14. For the enantioselective total synthesis of 1, see: (a) Akiyama, T.; Ohnari, M.; Shima, H.; Ozaki, S. Synlett 1991, 831-832. (b) Shing, T. K. M.; Tai, V. W.-F. J. Chem. Soc., Perkin Trans. 1 1994, 2017-2025. (c) McDevitt, R. E.; Fraser-Reid, B. J. Org. Chem. 1994, 59, 3250-3252. (d) Sato, K.; Bokura, M. ; Moriyama, H.; Igarashi, T. Chem. Lett. 1994, 37-40. (e) Jung, M. E.; Choe, S. W. T. J. Org. Chem. 1995, 60, 3280-3281. (f) Schlessinger, R. H.; Bergstrom, C. P. J. Org. Chem. 1995, 60, 16-17. (g) Letellier, P.; Ralainairina, R.; Beaupère, D.; Uzan, R. Synthesis 1997, 925-930. (h) Takahashi, H.; Iimori, T.; Ikegami, S. Tetahedron Lett. 1998, 39, 6939-6942. (i) Ziegler, F. E.; Wang, Y. J. Org. Chem. 1998, 63, 426-427; see also J. Org. Chem. 1998, 63, 7920-7930. (j) Trost, B. M.; Patterson, D. E.; Hembre, E. J. Chem. Eur. J. 2001, 7, 3768-3775.
15. For the enantioselective total synthesis of 1, see: (a) Akiyama, T.; Ohnari, M.; Shima, H.; Ozaki, S. Synlett 1991, 831-832. (b) Shing, T. K. M.; Tai, V. W.-F. J. Chem. Soc., Perkin Trans. 1 1994, 2017-2025. (c) McDevitt, R. E.; Fraser-Reid, B. J. Org. Chem. 1994, 59, 3250-3252. (d) Sato, K.; Bokura, M. ; Moriyama, H.; Igarashi, T. Chem. Lett. 1994, 37-40. (e) Jung, M. E.; Choe, S. W. T. J. Org. Chem. 1995, 60, 3280-3281. (f) Schlessinger, R. H.; Bergstrom, C. P. J. Org. Chem. 1995, 60, 16-17. (g) Letellier, P.; Ralainairina, R.; Beaupère, D.; Uzan, R. Synthesis 1997, 925-930. (h) Takahashi, H.; Iimori, T.; Ikegami, S. Tetahedron Lett. 1998, 39, 6939-6942. (i) Ziegler, F. E.; Wang, Y. J. Org. Chem. 1998, 63, 426-427; see also J. Org. Chem. 1998, 63, 7920-7930. (j) Trost, B. M.; Patterson, D. E.; Hembre, E. J. Chem. Eur. J. 2001, 7, 3768-3775.
16. For a review, see: Marco-Contelles, J. Eur. J. Org. Chem. 2001, 1607-1618.
17. In general, the Ferrier(II) cyclization has been used as a representative means for converting sugars to cyclitol derivatives; see: (a) Ferrier, R. J. J. Chem. Soc., Perkin Trans. 1 1979, 1455-1458; see also Chem. Rev. 1993, 93, 2779-2831.
18. In general, the Ferrier(II) cyclization has been used as a representative means for converting sugars to cyclitol derivatives; see: (a) Ferrier, R. J. J. Chem. Soc., Perkin Trans. 1 1979, 1455-1458; see also Chem. Rev. 1993, 93, 2779-2831. This reaction can provide a convenient way for converting 6-carbon sugars to 2,3,4,5-(tetrahydoxy)cyclohexanone derivatives. therefore, if additional substituents are required, they have to be introduced after the cyclization. Since this methods features oxy-mercuration as a key step, a more environmentally benign process using promoters other than mercury should be desirable, and some acceptable alternatives become available such as palladium(II)-catalyzed processes.
19. For these works, see: (b) Adam, S. Tetrahedron Lett. 1988, 29, 6589-6592 and ref 4h. A promising strategy capable of introducing a hydroxymethyl substituent concomitantly on converting a sugar to a cyclitol derivative was developed in Tatsuta's total synthesis of 1 (ref 3). In this case intramolecular nitrile oxide cycloaddition reaction played an important role for a series of transformations from expensive L-glucose to the desired cyclitol derivative.
20. For generation and intramolecular [3 + 2] cycloaddition reaction of silyl nitronate under the similar conditions, see the preceding paper in this issue. For a review for nitronate cycloadditions including silyl nitronates, see: Ono, N. The Nitro Group in Organic Synthesis; Wiley-VCH: New York, 2001; pp 267-274.
21. Bernet, von B.; Vasella, A. Helv. Chim. Acta 1979, 62, 1990-2015. A modified procedure for the synthesis of 2 is described in Supporting Information.
22. Saito, S.; Kuroda, A.; Tanaka, K.; Kimura, R. Synlett 1996, 231-233.
23. Simoni, D.; Invidiata, F. P.; Manfredini, S.; Ferroni, R.; Lampronti, I. ; Roberti, M.; Pollini, G. P. Tetrahedron Lett. 1997, 38, 2749-2752.
24. For related diastereoselective Henry reaction, see: Hanessian, S.; Kloss, J. Tetrahedron Lett. 1985, 26, 1261-1264. Other bases such as DBU or KF resulted in lower yield with diastereoselectivity lower than that of the TMG-catalyzed case.
25. No cycloaddition reaction proceeded at all when recovered 6b was subjected to the same reaction conditions as those for cycloaddition (footnote e in Scheme 2): 6b was recovered unchanged again in 66%, and the rest of 6b (34%) seemed to decompose or lead to a mixture of unidentifiable products.
26. Two possible mechanisms deserve consideration for such a geometrical isomerization of nitronates: one might involve a protonation-deprotonation process and the other might involve the 1,3-migration of a trimethylsilyl group from oxygen to oxygen. For discussion with respect to the 1,3-migration, see: Colvin, E. W.; Beck, A. K.; Bastani, B.; Seebach, D.; Dunitz, J. D. Helv. Chim. Acta 1980, 63, 697-710.
27. Nitta, M.; Yi, A.; Kobayashi, T. Bull. Chem. Soc. Jpn. 1985, 58, 991-994.
28. 4/CeCl/THF gave less selective results: yields of 12a and 12b were 16% and 13%, 22% and 11%, 49% and 20%, 44% and 15%, or 20% and 33%, respectively.
29. For a review for cleavage of cyclic ortho esters, see: Org. React. 1984, 30, 457-566.
30. All the products gave satisfactory spectroscopic data (NMR, IR, and MS). See Supporting Information.
31. 6-mediated deoxygenation reactions of this class is under investigation.
32. ( 19) Overall yield of 1 from 9 was 31% corresponding to the sum of two routes via 12a (19%) and 12b (12%).