Stereoselective Synthesis of Polyhydroxylated Indolizidines from γ-Hydroxy α,β-Unsaturated Sulfones

Journal of Organic Chemistry

Volumn 63, Issue 9, 1998, Pages 2993-3005

  Carretero, Juan C ^a   Arrayás, Ramón Gómez ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000512831     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo972167p     Document Type: Article

References (70)

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2. For some recent reviews and books, see: (a) Michael, J. P. Nat. Prod. Rep. 1997, 14, 619, (b) Elbein, A. D.; Molyneux, R. J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley-Interscience: New York, 1987; Vol. 5, Chapter 1. Howard, A. S.; Michael, J. P. in The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1986; Vol. 28, Chapter 3.
3. For some recent reviews and books, see: (a) Michael, J. P. Nat. Prod. Rep. 1997, 14, 619, (b) Elbein, A. D.; Molyneux, R. J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley-Interscience: New York, 1987; Vol. 5, Chapter 1. Howard, A. S.; Michael, J. P. in The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1986; Vol. 28, Chapter 3.
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11. For a review on the synthesis of castanospermine and stereoisomers, see: Burgess, K.; Henderson, I. Tetrahedron 1992, 48, 4045 and references therein. For recent references, see: (a) Bell, A. A.; Pickering, L.; Watson, A. A.; Nash, R. J.; Griffiths, R. C.; Jones, M. G.; Fleet, G. W. J. Tetrahedron Lett. 1996, 37, 8561. (b) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (c) Zhao, H.; Mootoo, A. R. J. Org. Chem. 1996, 61, 6762. (d) Martin, S. F.; Chen, H.-J.; Lynch, V. M. J. Org. Chem. 1995, 60, 276. (e) Furneaux, R. H.; Mason, J. M.; Tyler, P. C. Tetrahedron Lett. 1995, 36, 3055. (f) Leeper, F. J.; Howard, S. Tetrahedron Lett. 1995, 36, 2335. (g) Furneaux, R. H.; Mason, J. M.; Tyler, P. C. Tetrahedron Lett. 1994, 35, 3143. (h) Chen, Y.; Vogel, P. J. Org. Chem. 1994, 59, 2487. (i) Kim, N.-S.; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489. (j) Furneaux, R. H.; Gainsford, G. J.; Mason, J. M.; Tyler, P. C. Tetrahedron 1994, 50, 2131. (k) Casiraghi, G.; Ulgheri, F.; Spanu, P.; Rassu, G.; Pinna, L.; Fava, G. G.; Ferrari, M. B.; Pelosi, G. J. Chem. Soc., Perkin Trans. 1 1993, 2991. (l) Ina, H.; Kibayashi, C. J. Org. Chem. 1993, 58, 52. (m) Kim, N.-S.; Choi, J.-R.; Cha, J. K. J. Org. Chem. 1993, 58, 7096. (n) Siriwardena, A. H.; Chiaroni, A.; Riche, C.; Grierson, D. S. J. Org. Chem. 1992, 57, 5661.
12. For a review on the synthesis of castanospermine and stereoisomers, see: Burgess, K.; Henderson, I. Tetrahedron 1992, 48, 4045 and references therein. For recent references, see: (a) Bell, A. A.; Pickering, L.; Watson, A. A.; Nash, R. J.; Griffiths, R. C.; Jones, M. G.; Fleet, G. W. J. Tetrahedron Lett. 1996, 37, 8561. (b) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (c) Zhao, H.; Mootoo, A. R. J. Org. Chem. 1996, 61, 6762. (d) Martin, S. F.; Chen, H.-J.; Lynch, V. M. J. Org. Chem. 1995, 60, 276. (e) Furneaux, R. H.; Mason, J. M.; Tyler, P. C. Tetrahedron Lett. 1995, 36, 3055. (f) Leeper, F. J.; Howard, S. Tetrahedron Lett. 1995, 36, 2335. (g) Furneaux, R. H.; Mason, J. M.; Tyler, P. C. Tetrahedron Lett. 1994, 35, 3143. (h) Chen, Y.; Vogel, P. J. Org. Chem. 1994, 59, 2487. (i) Kim, N.-S.; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489. (j) Furneaux, R. H.; Gainsford, G. J.; Mason, J. M.; Tyler, P. C. Tetrahedron 1994, 50, 2131. (k) Casiraghi, G.; Ulgheri, F.; Spanu, P.; Rassu, G.; Pinna, L.; Fava, G. G.; Ferrari, M. B.; Pelosi, G. J. Chem. Soc., Perkin Trans. 1 1993, 2991. (l) Ina, H.; Kibayashi, C. J. Org. Chem. 1993, 58, 52. (m) Kim, N.-S.; Choi, J.-R.; Cha, J. K. J. Org. Chem. 1993, 58, 7096. (n) Siriwardena, A. H.; Chiaroni, A.; Riche, C.; Grierson, D. S. J. Org. Chem. 1992, 57, 5661.
13. For a review on the synthesis of castanospermine and stereoisomers, see: Burgess, K.; Henderson, I. Tetrahedron 1992, 48, 4045 and references therein. For recent references, see: (a) Bell, A. A.; Pickering, L.; Watson, A. A.; Nash, R. J.; Griffiths, R. C.; Jones, M. G.; Fleet, G. W. J. Tetrahedron Lett. 1996, 37, 8561. (b) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (c) Zhao, H.; Mootoo, A. R. J. Org. Chem. 1996, 61, 6762. (d) Martin, S. F.; Chen, H.-J.; Lynch, V. M. J. Org. Chem. 1995, 60, 276. (e) Furneaux, R. H.; Mason, J. M.; Tyler, P. C. Tetrahedron Lett. 1995, 36, 3055. (f) Leeper, F. J.; Howard, S. Tetrahedron Lett. 1995, 36, 2335. (g) Furneaux, R. H.; Mason, J. M.; Tyler, P. C. Tetrahedron Lett. 1994, 35, 3143. (h) Chen, Y.; Vogel, P. J. Org. Chem. 1994, 59, 2487. (i) Kim, N.-S.; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489. (j) Furneaux, R. H.; Gainsford, G. J.; Mason, J. M.; Tyler, P. C. Tetrahedron 1994, 50, 2131. (k) Casiraghi, G.; Ulgheri, F.; Spanu, P.; Rassu, G.; Pinna, L.; Fava, G. G.; Ferrari, M. B.; Pelosi, G. J. Chem. Soc., Perkin Trans. 1 1993, 2991. (l) Ina, H.; Kibayashi, C. J. Org. Chem. 1993, 58, 52. (m) Kim, N.-S.; Choi, J.-R.; Cha, J. K. J. Org. Chem. 1993, 58, 7096. (n) Siriwardena, A. H.; Chiaroni, A.; Riche, C.; Grierson, D. S. J. Org. Chem. 1992, 57, 5661.
14. For a review on the synthesis of castanospermine and stereoisomers, see: Burgess, K.; Henderson, I. Tetrahedron 1992, 48, 4045 and references therein. For recent references, see: (a) Bell, A. A.; Pickering, L.; Watson, A. A.; Nash, R. J.; Griffiths, R. C.; Jones, M. G.; Fleet, G. W. J. Tetrahedron Lett. 1996, 37, 8561. (b) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (c) Zhao, H.; Mootoo, A. R. J. Org. Chem. 1996, 61, 6762. (d) Martin, S. F.; Chen, H.-J.; Lynch, V. M. J. Org. Chem. 1995, 60, 276. (e) Furneaux, R. H.; Mason, J. M.; Tyler, P. C. Tetrahedron Lett. 1995, 36, 3055. (f) Leeper, F. J.; Howard, S. Tetrahedron Lett. 1995, 36, 2335. (g) Furneaux, R. H.; Mason, J. M.; Tyler, P. C. Tetrahedron Lett. 1994, 35, 3143. (h) Chen, Y.; Vogel, P. J. Org. Chem. 1994, 59, 2487. (i) Kim, N.-S.; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489. (j) Furneaux, R. H.; Gainsford, G. J.; Mason, J. M.; Tyler, P. C. Tetrahedron 1994, 50, 2131. (k) Casiraghi, G.; Ulgheri, F.; Spanu, P.; Rassu, G.; Pinna, L.; Fava, G. G.; Ferrari, M. B.; Pelosi, G. J. Chem. Soc., Perkin Trans. 1 1993, 2991. (l) Ina, H.; Kibayashi, C. J. Org. Chem. 1993, 58, 52. (m) Kim, N.-S.; Choi, J.-R.; Cha, J. K. J. Org. Chem. 1993, 58, 7096. (n) Siriwardena, A. H.; Chiaroni, A.; Riche, C.; Grierson, D. S. J. Org. Chem. 1992, 57, 5661.
15. For a review on the synthesis of castanospermine and stereoisomers, see: Burgess, K.; Henderson, I. Tetrahedron 1992, 48, 4045 and references therein. For recent references, see: (a) Bell, A. A.; Pickering, L.; Watson, A. A.; Nash, R. J.; Griffiths, R. C.; Jones, M. G.; Fleet, G. W. J. Tetrahedron Lett. 1996, 37, 8561. (b) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (c) Zhao, H.; Mootoo, A. R. J. Org. Chem. 1996, 61, 6762. (d) Martin, S. F.; Chen, H.-J.; Lynch, V. M. J. Org. Chem. 1995, 60, 276. (e) Furneaux, R. H.; Mason, J. M.; Tyler, P. C. Tetrahedron Lett. 1995, 36, 3055. (f) Leeper, F. J.; Howard, S. Tetrahedron Lett. 1995, 36, 2335. (g) Furneaux, R. H.; Mason, J. M.; Tyler, P. C. Tetrahedron Lett. 1994, 35, 3143. (h) Chen, Y.; Vogel, P. J. Org. Chem. 1994, 59, 2487. (i) Kim, N.-S.; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489. (j) Furneaux, R. H.; Gainsford, G. J.; Mason, J. M.; Tyler, P. C. Tetrahedron 1994, 50, 2131. (k) Casiraghi, G.; Ulgheri, F.; Spanu, P.; Rassu, G.; Pinna, L.; Fava, G. G.; Ferrari, M. B.; Pelosi, G. J. Chem. Soc., Perkin Trans. 1 1993, 2991. (l) Ina, H.; Kibayashi, C. J. Org. Chem. 1993, 58, 52. (m) Kim, N.-S.; Choi, J.-R.; Cha, J. K. J. Org. Chem. 1993, 58, 7096. (n) Siriwardena, A. H.; Chiaroni, A.; Riche, C.; Grierson, D. S. J. Org. Chem. 1992, 57, 5661.
16. For a review on the synthesis of castanospermine and stereoisomers, see: Burgess, K.; Henderson, I. Tetrahedron 1992, 48, 4045 and references therein. For recent references, see: (a) Bell, A. A.; Pickering, L.; Watson, A. A.; Nash, R. J.; Griffiths, R. C.; Jones, M. G.; Fleet, G. W. J. Tetrahedron Lett. 1996, 37, 8561. (b) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (c) Zhao, H.; Mootoo, A. R. J. Org. Chem. 1996, 61, 6762. (d) Martin, S. F.; Chen, H.-J.; Lynch, V. M. J. Org. Chem. 1995, 60, 276. (e) Furneaux, R. H.; Mason, J. M.; Tyler, P. C. Tetrahedron Lett. 1995, 36, 3055. (f) Leeper, F. J.; Howard, S. Tetrahedron Lett. 1995, 36, 2335. (g) Furneaux, R. H.; Mason, J. M.; Tyler, P. C. Tetrahedron Lett. 1994, 35, 3143. (h) Chen, Y.; Vogel, P. J. Org. Chem. 1994, 59, 2487. (i) Kim, N.-S.; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489. (j) Furneaux, R. H.; Gainsford, G. J.; Mason, J. M.; Tyler, P. C. Tetrahedron 1994, 50, 2131. (k) Casiraghi, G.; Ulgheri, F.; Spanu, P.; Rassu, G.; Pinna, L.; Fava, G. G.; Ferrari, M. B.; Pelosi, G. J. Chem. Soc., Perkin Trans. 1 1993, 2991. (l) Ina, H.; Kibayashi, C. J. Org. Chem. 1993, 58, 52. (m) Kim, N.-S.; Choi, J.-R.; Cha, J. K. J. Org. Chem. 1993, 58, 7096. (n) Siriwardena, A. H.; Chiaroni, A.; Riche, C.; Grierson, D. S. J. Org. Chem. 1992, 57, 5661.
17. For a review on the synthesis of castanospermine and stereoisomers, see: Burgess, K.; Henderson, I. Tetrahedron 1992, 48, 4045 and references therein. For recent references, see: (a) Bell, A. A.; Pickering, L.; Watson, A. A.; Nash, R. J.; Griffiths, R. C.; Jones, M. G.; Fleet, G. W. J. Tetrahedron Lett. 1996, 37, 8561. (b) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (c) Zhao, H.; Mootoo, A. R. J. Org. Chem. 1996, 61, 6762. (d) Martin, S. F.; Chen, H.-J.; Lynch, V. M. J. Org. Chem. 1995, 60, 276. (e) Furneaux, R. H.; Mason, J. M.; Tyler, P. C. Tetrahedron Lett. 1995, 36, 3055. (f) Leeper, F. J.; Howard, S. Tetrahedron Lett. 1995, 36, 2335. (g) Furneaux, R. H.; Mason, J. M.; Tyler, P. C. Tetrahedron Lett. 1994, 35, 3143. (h) Chen, Y.; Vogel, P. J. Org. Chem. 1994, 59, 2487. (i) Kim, N.-S.; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489. (j) Furneaux, R. H.; Gainsford, G. J.; Mason, J. M.; Tyler, P. C. Tetrahedron 1994, 50, 2131. (k) Casiraghi, G.; Ulgheri, F.; Spanu, P.; Rassu, G.; Pinna, L.; Fava, G. G.; Ferrari, M. B.; Pelosi, G. J. Chem. Soc., Perkin Trans. 1 1993, 2991. (l) Ina, H.; Kibayashi, C. J. Org. Chem. 1993, 58, 52. (m) Kim, N.-S.; Choi, J.-R.; Cha, J. K. J. Org. Chem. 1993, 58, 7096. (n) Siriwardena, A. H.; Chiaroni, A.; Riche, C.; Grierson, D. S. J. Org. Chem. 1992, 57, 5661.
18. For a review on the synthesis of castanospermine and stereoisomers, see: Burgess, K.; Henderson, I. Tetrahedron 1992, 48, 4045 and references therein. For recent references, see: (a) Bell, A. A.; Pickering, L.; Watson, A. A.; Nash, R. J.; Griffiths, R. C.; Jones, M. G.; Fleet, G. W. J. Tetrahedron Lett. 1996, 37, 8561. (b) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (c) Zhao, H.; Mootoo, A. R. J. Org. Chem. 1996, 61, 6762. (d) Martin, S. F.; Chen, H.-J.; Lynch, V. M. J. Org. Chem. 1995, 60, 276. (e) Furneaux, R. H.; Mason, J. M.; Tyler, P. C. Tetrahedron Lett. 1995, 36, 3055. (f) Leeper, F. J.; Howard, S. Tetrahedron Lett. 1995, 36, 2335. (g) Furneaux, R. H.; Mason, J. M.; Tyler, P. C. Tetrahedron Lett. 1994, 35, 3143. (h) Chen, Y.; Vogel, P. J. Org. Chem. 1994, 59, 2487. (i) Kim, N.-S.; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489. (j) Furneaux, R. H.; Gainsford, G. J.; Mason, J. M.; Tyler, P. C. Tetrahedron 1994, 50, 2131. (k) Casiraghi, G.; Ulgheri, F.; Spanu, P.; Rassu, G.; Pinna, L.; Fava, G. G.; Ferrari, M. B.; Pelosi, G. J. Chem. Soc., Perkin Trans. 1 1993, 2991. (l) Ina, H.; Kibayashi, C. J. Org. Chem. 1993, 58, 52. (m) Kim, N.-S.; Choi, J.-R.; Cha, J. K. J. Org. Chem. 1993, 58, 7096. (n) Siriwardena, A. H.; Chiaroni, A.; Riche, C.; Grierson, D. S. J. Org. Chem. 1992, 57, 5661.
19. For a review on the synthesis of castanospermine and stereoisomers, see: Burgess, K.; Henderson, I. Tetrahedron 1992, 48, 4045 and references therein. For recent references, see: (a) Bell, A. A.; Pickering, L.; Watson, A. A.; Nash, R. J.; Griffiths, R. C.; Jones, M. G.; Fleet, G. W. J. Tetrahedron Lett. 1996, 37, 8561. (b) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (c) Zhao, H.; Mootoo, A. R. J. Org. Chem. 1996, 61, 6762. (d) Martin, S. F.; Chen, H.-J.; Lynch, V. M. J. Org. Chem. 1995, 60, 276. (e) Furneaux, R. H.; Mason, J. M.; Tyler, P. C. Tetrahedron Lett. 1995, 36, 3055. (f) Leeper, F. J.; Howard, S. Tetrahedron Lett. 1995, 36, 2335. (g) Furneaux, R. H.; Mason, J. M.; Tyler, P. C. Tetrahedron Lett. 1994, 35, 3143. (h) Chen, Y.; Vogel, P. J. Org. Chem. 1994, 59, 2487. (i) Kim, N.-S.; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489. (j) Furneaux, R. H.; Gainsford, G. J.; Mason, J. M.; Tyler, P. C. Tetrahedron 1994, 50, 2131. (k) Casiraghi, G.; Ulgheri, F.; Spanu, P.; Rassu, G.; Pinna, L.; Fava, G. G.; Ferrari, M. B.; Pelosi, G. J. Chem. Soc., Perkin Trans. 1 1993, 2991. (l) Ina, H.; Kibayashi, C. J. Org. Chem. 1993, 58, 52. (m) Kim, N.-S.; Choi, J.-R.; Cha, J. K. J. Org. Chem. 1993, 58, 7096. (n) Siriwardena, A. H.; Chiaroni, A.; Riche, C.; Grierson, D. S. J. Org. Chem. 1992, 57, 5661.
20. For a review on the synthesis of castanospermine and stereoisomers, see: Burgess, K.; Henderson, I. Tetrahedron 1992, 48, 4045 and references therein. For recent references, see: (a) Bell, A. A.; Pickering, L.; Watson, A. A.; Nash, R. J.; Griffiths, R. C.; Jones, M. G.; Fleet, G. W. J. Tetrahedron Lett. 1996, 37, 8561. (b) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (c) Zhao, H.; Mootoo, A. R. J. Org. Chem. 1996, 61, 6762. (d) Martin, S. F.; Chen, H.-J.; Lynch, V. M. J. Org. Chem. 1995, 60, 276. (e) Furneaux, R. H.; Mason, J. M.; Tyler, P. C. Tetrahedron Lett. 1995, 36, 3055. (f) Leeper, F. J.; Howard, S. Tetrahedron Lett. 1995, 36, 2335. (g) Furneaux, R. H.; Mason, J. M.; Tyler, P. C. Tetrahedron Lett. 1994, 35, 3143. (h) Chen, Y.; Vogel, P. J. Org. Chem. 1994, 59, 2487. (i) Kim, N.-S.; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489. (j) Furneaux, R. H.; Gainsford, G. J.; Mason, J. M.; Tyler, P. C. Tetrahedron 1994, 50, 2131. (k) Casiraghi, G.; Ulgheri, F.; Spanu, P.; Rassu, G.; Pinna, L.; Fava, G. G.; Ferrari, M. B.; Pelosi, G. J. Chem. Soc., Perkin Trans. 1 1993, 2991. (l) Ina, H.; Kibayashi, C. J. Org. Chem. 1993, 58, 52. (m) Kim, N.-S.; Choi, J.-R.; Cha, J. K. J. Org. Chem. 1993, 58, 7096. (n) Siriwardena, A. H.; Chiaroni, A.; Riche, C.; Grierson, D. S. J. Org. Chem. 1992, 57, 5661.
21. For a review on the synthesis of castanospermine and stereoisomers, see: Burgess, K.; Henderson, I. Tetrahedron 1992, 48, 4045 and references therein. For recent references, see: (a) Bell, A. A.; Pickering, L.; Watson, A. A.; Nash, R. J.; Griffiths, R. C.; Jones, M. G.; Fleet, G. W. J. Tetrahedron Lett. 1996, 37, 8561. (b) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (c) Zhao, H.; Mootoo, A. R. J. Org. Chem. 1996, 61, 6762. (d) Martin, S. F.; Chen, H.-J.; Lynch, V. M. J. Org. Chem. 1995, 60, 276. (e) Furneaux, R. H.; Mason, J. M.; Tyler, P. C. Tetrahedron Lett. 1995, 36, 3055. (f) Leeper, F. J.; Howard, S. Tetrahedron Lett. 1995, 36, 2335. (g) Furneaux, R. H.; Mason, J. M.; Tyler, P. C. Tetrahedron Lett. 1994, 35, 3143. (h) Chen, Y.; Vogel, P. J. Org. Chem. 1994, 59, 2487. (i) Kim, N.-S.; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489. (j) Furneaux, R. H.; Gainsford, G. J.; Mason, J. M.; Tyler, P. C. Tetrahedron 1994, 50, 2131. (k) Casiraghi, G.; Ulgheri, F.; Spanu, P.; Rassu, G.; Pinna, L.; Fava, G. G.; Ferrari, M. B.; Pelosi, G. J. Chem. Soc., Perkin Trans. 1 1993, 2991. (l) Ina, H.; Kibayashi, C. J. Org. Chem. 1993, 58, 52. (m) Kim, N.-S.; Choi, J.-R.; Cha, J. K. J. Org. Chem. 1993, 58, 7096. (n) Siriwardena, A. H.; Chiaroni, A.; Riche, C.; Grierson, D. S. J. Org. Chem. 1992, 57, 5661.
22. For a review on the synthesis of castanospermine and stereoisomers, see: Burgess, K.; Henderson, I. Tetrahedron 1992, 48, 4045 and references therein. For recent references, see: (a) Bell, A. A.; Pickering, L.; Watson, A. A.; Nash, R. J.; Griffiths, R. C.; Jones, M. G.; Fleet, G. W. J. Tetrahedron Lett. 1996, 37, 8561. (b) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (c) Zhao, H.; Mootoo, A. R. J. Org. Chem. 1996, 61, 6762. (d) Martin, S. F.; Chen, H.-J.; Lynch, V. M. J. Org. Chem. 1995, 60, 276. (e) Furneaux, R. H.; Mason, J. M.; Tyler, P. C. Tetrahedron Lett. 1995, 36, 3055. (f) Leeper, F. J.; Howard, S. Tetrahedron Lett. 1995, 36, 2335. (g) Furneaux, R. H.; Mason, J. M.; Tyler, P. C. Tetrahedron Lett. 1994, 35, 3143. (h) Chen, Y.; Vogel, P. J. Org. Chem. 1994, 59, 2487. (i) Kim, N.-S.; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489. (j) Furneaux, R. H.; Gainsford, G. J.; Mason, J. M.; Tyler, P. C. Tetrahedron 1994, 50, 2131. (k) Casiraghi, G.; Ulgheri, F.; Spanu, P.; Rassu, G.; Pinna, L.; Fava, G. G.; Ferrari, M. B.; Pelosi, G. J. Chem. Soc., Perkin Trans. 1 1993, 2991. (l) Ina, H.; Kibayashi, C. J. Org. Chem. 1993, 58, 52. (m) Kim, N.-S.; Choi, J.-R.; Cha, J. K. J. Org. Chem. 1993, 58, 7096. (n) Siriwardena, A. H.; Chiaroni, A.; Riche, C.; Grierson, D. S. J. Org. Chem. 1992, 57, 5661.
23. For a review on the synthesis of castanospermine and stereoisomers, see: Burgess, K.; Henderson, I. Tetrahedron 1992, 48, 4045 and references therein. For recent references, see: (a) Bell, A. A.; Pickering, L.; Watson, A. A.; Nash, R. J.; Griffiths, R. C.; Jones, M. G.; Fleet, G. W. J. Tetrahedron Lett. 1996, 37, 8561. (b) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (c) Zhao, H.; Mootoo, A. R. J. Org. Chem. 1996, 61, 6762. (d) Martin, S. F.; Chen, H.-J.; Lynch, V. M. J. Org. Chem. 1995, 60, 276. (e) Furneaux, R. H.; Mason, J. M.; Tyler, P. C. Tetrahedron Lett. 1995, 36, 3055. (f) Leeper, F. J.; Howard, S. Tetrahedron Lett. 1995, 36, 2335. (g) Furneaux, R. H.; Mason, J. M.; Tyler, P. C. Tetrahedron Lett. 1994, 35, 3143. (h) Chen, Y.; Vogel, P. J. Org. Chem. 1994, 59, 2487. (i) Kim, N.-S.; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489. (j) Furneaux, R. H.; Gainsford, G. J.; Mason, J. M.; Tyler, P. C. Tetrahedron 1994, 50, 2131. (k) Casiraghi, G.; Ulgheri, F.; Spanu, P.; Rassu, G.; Pinna, L.; Fava, G. G.; Ferrari, M. B.; Pelosi, G. J. Chem. Soc., Perkin Trans. 1 1993, 2991. (l) Ina, H.; Kibayashi, C. J. Org. Chem. 1993, 58, 52. (m) Kim, N.-S.; Choi, J.-R.; Cha, J. K. J. Org. Chem. 1993, 58, 7096. (n) Siriwardena, A. H.; Chiaroni, A.; Riche, C.; Grierson, D. S. J. Org. Chem. 1992, 57, 5661.
24. For a review on the synthesis of castanospermine and stereoisomers, see: Burgess, K.; Henderson, I. Tetrahedron 1992, 48, 4045 and references therein. For recent references, see: (a) Bell, A. A.; Pickering, L.; Watson, A. A.; Nash, R. J.; Griffiths, R. C.; Jones, M. G.; Fleet, G. W. J. Tetrahedron Lett. 1996, 37, 8561. (b) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (c) Zhao, H.; Mootoo, A. R. J. Org. Chem. 1996, 61, 6762. (d) Martin, S. F.; Chen, H.-J.; Lynch, V. M. J. Org. Chem. 1995, 60, 276. (e) Furneaux, R. H.; Mason, J. M.; Tyler, P. C. Tetrahedron Lett. 1995, 36, 3055. (f) Leeper, F. J.; Howard, S. Tetrahedron Lett. 1995, 36, 2335. (g) Furneaux, R. H.; Mason, J. M.; Tyler, P. C. Tetrahedron Lett. 1994, 35, 3143. (h) Chen, Y.; Vogel, P. J. Org. Chem. 1994, 59, 2487. (i) Kim, N.-S.; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489. (j) Furneaux, R. H.; Gainsford, G. J.; Mason, J. M.; Tyler, P. C. Tetrahedron 1994, 50, 2131. (k) Casiraghi, G.; Ulgheri, F.; Spanu, P.; Rassu, G.; Pinna, L.; Fava, G. G.; Ferrari, M. B.; Pelosi, G. J. Chem. Soc., Perkin Trans. 1 1993, 2991. (l) Ina, H.; Kibayashi, C. J. Org. Chem. 1993, 58, 52. (m) Kim, N.-S.; Choi, J.-R.; Cha, J. K. J. Org. Chem. 1993, 58, 7096. (n) Siriwardena, A. H.; Chiaroni, A.; Riche, C.; Grierson, D. S. J. Org. Chem. 1992, 57, 5661.
25. For some recent references on the synthesis of swainsonine and analogues, see: (a) Hunt, J. A.; Roush, W. R. J. Org. Chem. 1997, 62, 1112. (b) Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 7217. (c) Zhou, W. S.; Xie, W.-G.; Lu, Z.-H.; Pan, X.-F. J. Chem. Soc., Perkin Trans. 1 1995, 2599. (d) Angermann, J.; Homann, K.; Reissig, H.-U.; Zimmer, R. Synlett 1995, 1014. (e) Oishi, T.; Iwakura, T.; Hirama, M.; Ito S. Synlett 1995, 404. (f) Rang, S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049. (g) Zhou, W.-S.; Xie, W. G.; Lu, Z.-H.; Pan, X.-F. Tetrahedron Lett. 1995, 36, 1291. (h) Hunt, J. A.; Roush, W. R. Tetrahedron Lett. 1995, 36, 501. (i) Honda, T.; Hoshi, M.; Kanal, K.; Tsubuki, M. J. Chem. Soc., Perkin Trans. 1 1994, 2091. (j) Naruse, M.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1994, 59, 1358.
26. For some recent references on the synthesis of swainsonine and analogues, see: (a) Hunt, J. A.; Roush, W. R. J. Org. Chem. 1997, 62, 1112. (b) Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 7217. (c) Zhou, W. S.; Xie, W.-G.; Lu, Z.-H.; Pan, X.-F. J. Chem. Soc., Perkin Trans. 1 1995, 2599. (d) Angermann, J.; Homann, K.; Reissig, H.-U.; Zimmer, R. Synlett 1995, 1014. (e) Oishi, T.; Iwakura, T.; Hirama, M.; Ito S. Synlett 1995, 404. (f) Rang, S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049. (g) Zhou, W.-S.; Xie, W. G.; Lu, Z.-H.; Pan, X.-F. Tetrahedron Lett. 1995, 36, 1291. (h) Hunt, J. A.; Roush, W. R. Tetrahedron Lett. 1995, 36, 501. (i) Honda, T.; Hoshi, M.; Kanal, K.; Tsubuki, M. J. Chem. Soc., Perkin Trans. 1 1994, 2091. (j) Naruse, M.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1994, 59, 1358.
27. For some recent references on the synthesis of swainsonine and analogues, see: (a) Hunt, J. A.; Roush, W. R. J. Org. Chem. 1997, 62, 1112. (b) Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 7217. (c) Zhou, W. S.; Xie, W.-G.; Lu, Z.-H.; Pan, X.-F. J. Chem. Soc., Perkin Trans. 1 1995, 2599. (d) Angermann, J.; Homann, K.; Reissig, H.-U.; Zimmer, R. Synlett 1995, 1014. (e) Oishi, T.; Iwakura, T.; Hirama, M.; Ito S. Synlett 1995, 404. (f) Rang, S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049. (g) Zhou, W.-S.; Xie, W. G.; Lu, Z.-H.; Pan, X.-F. Tetrahedron Lett. 1995, 36, 1291. (h) Hunt, J. A.; Roush, W. R. Tetrahedron Lett. 1995, 36, 501. (i) Honda, T.; Hoshi, M.; Kanal, K.; Tsubuki, M. J. Chem. Soc., Perkin Trans. 1 1994, 2091. (j) Naruse, M.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1994, 59, 1358.
28. For some recent references on the synthesis of swainsonine and analogues, see: (a) Hunt, J. A.; Roush, W. R. J. Org. Chem. 1997, 62, 1112. (b) Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 7217. (c) Zhou, W. S.; Xie, W.-G.; Lu, Z.-H.; Pan, X.-F. J. Chem. Soc., Perkin Trans. 1 1995, 2599. (d) Angermann, J.; Homann, K.; Reissig, H.-U.; Zimmer, R. Synlett 1995, 1014. (e) Oishi, T.; Iwakura, T.; Hirama, M.; Ito S. Synlett 1995, 404. (f) Rang, S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049. (g) Zhou, W.-S.; Xie, W. G.; Lu, Z.-H.; Pan, X.-F. Tetrahedron Lett. 1995, 36, 1291. (h) Hunt, J. A.; Roush, W. R. Tetrahedron Lett. 1995, 36, 501. (i) Honda, T.; Hoshi, M.; Kanal, K.; Tsubuki, M. J. Chem. Soc., Perkin Trans. 1 1994, 2091. (j) Naruse, M.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1994, 59, 1358.
29. For some recent references on the synthesis of swainsonine and analogues, see: (a) Hunt, J. A.; Roush, W. R. J. Org. Chem. 1997, 62, 1112. (b) Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 7217. (c) Zhou, W. S.; Xie, W.-G.; Lu, Z.-H.; Pan, X.-F. J. Chem. Soc., Perkin Trans. 1 1995, 2599. (d) Angermann, J.; Homann, K.; Reissig, H.-U.; Zimmer, R. Synlett 1995, 1014. (e) Oishi, T.; Iwakura, T.; Hirama, M.; Ito S. Synlett 1995, 404. (f) Rang, S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049. (g) Zhou, W.-S.; Xie, W. G.; Lu, Z.-H.; Pan, X.-F. Tetrahedron Lett. 1995, 36, 1291. (h) Hunt, J. A.; Roush, W. R. Tetrahedron Lett. 1995, 36, 501. (i) Honda, T.; Hoshi, M.; Kanal, K.; Tsubuki, M. J. Chem. Soc., Perkin Trans. 1 1994, 2091. (j) Naruse, M.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1994, 59, 1358.
30. For some recent references on the synthesis of swainsonine and analogues, see: (a) Hunt, J. A.; Roush, W. R. J. Org. Chem. 1997, 62, 1112. (b) Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 7217. (c) Zhou, W. S.; Xie, W.-G.; Lu, Z.-H.; Pan, X.-F. J. Chem. Soc., Perkin Trans. 1 1995, 2599. (d) Angermann, J.; Homann, K.; Reissig, H.-U.; Zimmer, R. Synlett 1995, 1014. (e) Oishi, T.; Iwakura, T.; Hirama, M.; Ito S. Synlett 1995, 404. (f) Rang, S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049. (g) Zhou, W.-S.; Xie, W. G.; Lu, Z.-H.; Pan, X.-F. Tetrahedron Lett. 1995, 36, 1291. (h) Hunt, J. A.; Roush, W. R. Tetrahedron Lett. 1995, 36, 501. (i) Honda, T.; Hoshi, M.; Kanal, K.; Tsubuki, M. J. Chem. Soc., Perkin Trans. 1 1994, 2091. (j) Naruse, M.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1994, 59, 1358.
31. For some recent references on the synthesis of swainsonine and analogues, see: (a) Hunt, J. A.; Roush, W. R. J. Org. Chem. 1997, 62, 1112. (b) Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 7217. (c) Zhou, W. S.; Xie, W.-G.; Lu, Z.-H.; Pan, X.-F. J. Chem. Soc., Perkin Trans. 1 1995, 2599. (d) Angermann, J.; Homann, K.; Reissig, H.-U.; Zimmer, R. Synlett 1995, 1014. (e) Oishi, T.; Iwakura, T.; Hirama, M.; Ito S. Synlett 1995, 404. (f) Rang, S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049. (g) Zhou, W.-S.; Xie, W. G.; Lu, Z.-H.; Pan, X.-F. Tetrahedron Lett. 1995, 36, 1291. (h) Hunt, J. A.; Roush, W. R. Tetrahedron Lett. 1995, 36, 501. (i) Honda, T.; Hoshi, M.; Kanal, K.; Tsubuki, M. J. Chem. Soc., Perkin Trans. 1 1994, 2091. (j) Naruse, M.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1994, 59, 1358.
32. For some recent references on the synthesis of swainsonine and analogues, see: (a) Hunt, J. A.; Roush, W. R. J. Org. Chem. 1997, 62, 1112. (b) Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 7217. (c) Zhou, W. S.; Xie, W.-G.; Lu, Z.-H.; Pan, X.-F. J. Chem. Soc., Perkin Trans. 1 1995, 2599. (d) Angermann, J.; Homann, K.; Reissig, H.-U.; Zimmer, R. Synlett 1995, 1014. (e) Oishi, T.; Iwakura, T.; Hirama, M.; Ito S. Synlett 1995, 404. (f) Rang, S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049. (g) Zhou, W.-S.; Xie, W. G.; Lu, Z.-H.; Pan, X.-F. Tetrahedron Lett. 1995, 36, 1291. (h) Hunt, J. A.; Roush, W. R. Tetrahedron Lett. 1995, 36, 501. (i) Honda, T.; Hoshi, M.; Kanal, K.; Tsubuki, M. J. Chem. Soc., Perkin Trans. 1 1994, 2091. (j) Naruse, M.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1994, 59, 1358.
33. For some recent references on the synthesis of swainsonine and analogues, see: (a) Hunt, J. A.; Roush, W. R. J. Org. Chem. 1997, 62, 1112. (b) Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 7217. (c) Zhou, W. S.; Xie, W.-G.; Lu, Z.-H.; Pan, X.-F. J. Chem. Soc., Perkin Trans. 1 1995, 2599. (d) Angermann, J.; Homann, K.; Reissig, H.-U.; Zimmer, R. Synlett 1995, 1014. (e) Oishi, T.; Iwakura, T.; Hirama, M.; Ito S. Synlett 1995, 404. (f) Rang, S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049. (g) Zhou, W.-S.; Xie, W. G.; Lu, Z.-H.; Pan, X.-F. Tetrahedron Lett. 1995, 36, 1291. (h) Hunt, J. A.; Roush, W. R. Tetrahedron Lett. 1995, 36, 501. (i) Honda, T.; Hoshi, M.; Kanal, K.; Tsubuki, M. J. Chem. Soc., Perkin Trans. 1 1994, 2091. (j) Naruse, M.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1994, 59, 1358.
34. For some recent references on the synthesis of swainsonine and analogues, see: (a) Hunt, J. A.; Roush, W. R. J. Org. Chem. 1997, 62, 1112. (b) Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 7217. (c) Zhou, W. S.; Xie, W.-G.; Lu, Z.-H.; Pan, X.-F. J. Chem. Soc., Perkin Trans. 1 1995, 2599. (d) Angermann, J.; Homann, K.; Reissig, H.-U.; Zimmer, R. Synlett 1995, 1014. (e) Oishi, T.; Iwakura, T.; Hirama, M.; Ito S. Synlett 1995, 404. (f) Rang, S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049. (g) Zhou, W.-S.; Xie, W. G.; Lu, Z.-H.; Pan, X.-F. Tetrahedron Lett. 1995, 36, 1291. (h) Hunt, J. A.; Roush, W. R. Tetrahedron Lett. 1995, 36, 501. (i) Honda, T.; Hoshi, M.; Kanal, K.; Tsubuki, M. J. Chem. Soc., Perkin Trans. 1 1994, 2091. (j) Naruse, M.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1994, 59, 1358.
35. For recent references on the synthesis of lentiginosine and analogues, see: (a) Goti, A.; Cardona, F.; Brandi, A. Synlett 1996, 761. (b) Goti, A.; Cardona, F.; Brandi, A.; Picasso, S.; Vogel, P. Tetrahedron: Asymmetry 1996, 7, 1659. (c) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. (d) Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem 1995, 60, 6806. (e) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. (f) Cordero, F. M.; Cicchi, S.; Goti, A.; Brandi, A. Tetrahedron Lett. 1994, 35, 949. (g) Gurjar, M. K.; Ghost, L.; Syamala, M.; Jayasree, V. Tetrahedron Lett. 1994, 35, 8871.
36. For recent references on the synthesis of lentiginosine and analogues, see: (a) Goti, A.; Cardona, F.; Brandi, A. Synlett 1996, 761. (b) Goti, A.; Cardona, F.; Brandi, A.; Picasso, S.; Vogel, P. Tetrahedron: Asymmetry 1996, 7, 1659. (c) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. (d) Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem 1995, 60, 6806. (e) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. (f) Cordero, F. M.; Cicchi, S.; Goti, A.; Brandi, A. Tetrahedron Lett. 1994, 35, 949. (g) Gurjar, M. K.; Ghost, L.; Syamala, M.; Jayasree, V. Tetrahedron Lett. 1994, 35, 8871.
37. For recent references on the synthesis of lentiginosine and analogues, see: (a) Goti, A.; Cardona, F.; Brandi, A. Synlett 1996, 761. (b) Goti, A.; Cardona, F.; Brandi, A.; Picasso, S.; Vogel, P. Tetrahedron: Asymmetry 1996, 7, 1659. (c) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. (d) Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem 1995, 60, 6806. (e) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. (f) Cordero, F. M.; Cicchi, S.; Goti, A.; Brandi, A. Tetrahedron Lett. 1994, 35, 949. (g) Gurjar, M. K.; Ghost, L.; Syamala, M.; Jayasree, V. Tetrahedron Lett. 1994, 35, 8871.
38. For recent references on the synthesis of lentiginosine and analogues, see: (a) Goti, A.; Cardona, F.; Brandi, A. Synlett 1996, 761. (b) Goti, A.; Cardona, F.; Brandi, A.; Picasso, S.; Vogel, P. Tetrahedron: Asymmetry 1996, 7, 1659. (c) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. (d) Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem 1995, 60, 6806. (e) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. (f) Cordero, F. M.; Cicchi, S.; Goti, A.; Brandi, A. Tetrahedron Lett. 1994, 35, 949. (g) Gurjar, M. K.; Ghost, L.; Syamala, M.; Jayasree, V. Tetrahedron Lett. 1994, 35, 8871.
39. For recent references on the synthesis of lentiginosine and analogues, see: (a) Goti, A.; Cardona, F.; Brandi, A. Synlett 1996, 761. (b) Goti, A.; Cardona, F.; Brandi, A.; Picasso, S.; Vogel, P. Tetrahedron: Asymmetry 1996, 7, 1659. (c) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. (d) Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem 1995, 60, 6806. (e) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. (f) Cordero, F. M.; Cicchi, S.; Goti, A.; Brandi, A. Tetrahedron Lett. 1994, 35, 949. (g) Gurjar, M. K.; Ghost, L.; Syamala, M.; Jayasree, V. Tetrahedron Lett. 1994, 35, 8871.
40. For recent references on the synthesis of lentiginosine and analogues, see: (a) Goti, A.; Cardona, F.; Brandi, A. Synlett 1996, 761. (b) Goti, A.; Cardona, F.; Brandi, A.; Picasso, S.; Vogel, P. Tetrahedron: Asymmetry 1996, 7, 1659. (c) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. (d) Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem 1995, 60, 6806. (e) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. (f) Cordero, F. M.; Cicchi, S.; Goti, A.; Brandi, A. Tetrahedron Lett. 1994, 35, 949. (g) Gurjar, M. K.; Ghost, L.; Syamala, M.; Jayasree, V. Tetrahedron Lett. 1994, 35, 8871.
41. For recent references on the synthesis of lentiginosine and analogues, see: (a) Goti, A.; Cardona, F.; Brandi, A. Synlett 1996, 761. (b) Goti, A.; Cardona, F.; Brandi, A.; Picasso, S.; Vogel, P. Tetrahedron: Asymmetry 1996, 7, 1659. (c) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. (d) Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem 1995, 60, 6806. (e) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. (f) Cordero, F. M.; Cicchi, S.; Goti, A.; Brandi, A. Tetrahedron Lett. 1994, 35, 949. (g) Gurjar, M. K.; Ghost, L.; Syamala, M.; Jayasree, V. Tetrahedron Lett. 1994, 35, 8871.
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45. Winkler, D. A.; Holan, G. J. Med. Chem. 1988, 32, 2084.
46. (a) Adrio, J.; Carretero, J. C.; Gómez Arrayás, R. Synlett. 1996, 640
47. (b) De Blas, J.; Carretero, J. C.; Domínguez, E. Tetrahedron: Asymmetry 1995, 5, 1035.
48. Domínguez, E.; Carretero, J. C. Tetrahedron 1994, 50, 7557.
49. De Bias, J.; Carretero, J. C.; Domínguez, E. Tetrahedron Lett. 1994, 35, 4603.
50. (e) Carretero, J. C.; Domínguez, E. J. Org. Chem. 1993, 58, 1596.
51. For previous communications, see: (a) Carretero, J. C.; Gómez Arrayás, R.; Storch de Gracia, I. Tetrahedron Lett. 1996, 37, 3379. (b) Carretero, J. C.; Gómez Arrayás, R. J. Org. Chem. 1995, 60, 6000.
52. For previous communications, see: (a) Carretero, J. C.; Gómez Arrayás, R.; Storch de Gracia, I. Tetrahedron Lett. 1996, 37, 3379. (b) Carretero, J. C.; Gómez Arrayás, R. J. Org. Chem. 1995, 60, 6000.
53. For the preparation of (±)-γ-hydroxy-αβ-unsaturated sulfones, see: (a) Domínguez, E.; Carretero, J. C. Tetrahedron 1990, 46, 7197. (b) Trost, B. M.; Grese, T. A. J. Org. Chem. 1991, 56, 3189. For the synthesis of enantiomerically pure γ-hydroxy α,β-unsaturated sulfones, see: Carretero, J. C.; Domínguez, E. J. Org. Chem. 1992, 57, 3867.
54. For the preparation of (±)-γ-hydroxy-αβ-unsaturated sulfones, see: (a) Domínguez, E.; Carretero, J. C. Tetrahedron 1990, 46, 7197. (b) Trost, B. M.; Grese, T. A. J. Org. Chem. 1991, 56, 3189. For the synthesis of enantiomerically pure γ-hydroxy α,β-unsaturated sulfones, see: Carretero, J. C.; Domínguez, E. J. Org. Chem. 1992, 57, 3867.
55. For the preparation of (±)-γ-hydroxy-αβ-unsaturated sulfones, see: (a) Domínguez, E.; Carretero, J. C. Tetrahedron 1990, 46, 7197. (b) Trost, B. M.; Grese, T. A. J. Org. Chem. 1991, 56, 3189. For the synthesis of enantiomerically pure γ-hydroxy α,β-unsaturated sulfones, see: Carretero, J. C.; Domínguez, E. J. Org. Chem. 1992, 57, 3867.
56. 2,3- trans ≈ 2.5 Hz). Furthermore, the NOESY spectra of cis-5d and trans- 5d are in fully agreement with this assignment (see below). Chemical equation presented.
57. β,γ = 3.0 Hz). We assume that this conformational preference would act in an opposite sense to the steric effects discussed in Scheme 3, because it would favor the transition state C (conformationally similar to E) to a larger extent than D (conformationally similar to F). This conformational effect could explain why in the case of the hydroxy derivatives 3a and 4a-the substrates besides with the sterically least demanding OR group - their cyclizations gave predominantly the pyrrolidines of cis configuration. For conformational analysis in allylic alcohols and derivatives, see: Gung, B. W.; Melnick, J. P.; Wolf, M. A.; King, A. J. Org. Chem. 1995, 60, 1947. Chemical equation presented.
58. The use of the stereochemical terms cis and trans refers to the H(1)/H(8a) relationship.
59. Unexpectedly, the use of other bases such as LDA led to the formation of mixtures of products.
60. 1H NMR and NOESY spectra of their hydroxy derivatives 8, acetate of 9 (9-OAc), and 19 (see below). Chemical equation presented.
61. For a general study on the stereoselectivity of the reduction of conformationally restrained 2-sulfonylcyclohexanones, see: Carreño, J. C.; Domínguez, E.; Garcia Ruano, J. L.; Rubio, A. J. Org. Chem. 1987, 52, 3619.
62. 8a in anti relationship).
63. 2/t-BuOOH (cat.), complex mixtures of products were obtained.
64. The attempts to perform directly the synthesis of 27-29 in one step by double alkylation of 6d with 3-chloro-2-(chloromethyl)propene in the presence of 2 equiv of n-BuLi were unfruitful. For direct dialkylation of β-nitrogenated sulfones, see: (a) Alonso, D. A.; Costa, A.; Mancheño, B.; Nájera, C. Tetrahedron 1997, 53, 4791. (b) Caturla, F.; Nájera, C. Tetrahedron Lett. 1997, 38, 3789.
65. The attempts to perform directly the synthesis of 27-29 in one step by double alkylation of 6d with 3-chloro-2-(chloromethyl)propene in the presence of 2 equiv of n-BuLi were unfruitful. For direct dialkylation of β-nitrogenated sulfones, see: (a) Alonso, D. A.; Costa, A.; Mancheño, B.; Nájera, C. Tetrahedron 1997, 53, 4791. (b) Caturla, F.; Nájera, C. Tetrahedron Lett. 1997, 38, 3789.
66. Pearson, W. H.; Bergmeier, S. C.; Williams, J. P. J. Org. Chem. 1992, 57, 3977.
67. 3N). However, mainly due to an incomplete regioselectivity in the opening of the epoxide, and the rather different reactivity exhibited by each stereoisomer of the resulting mixture of hydroxy sulfones, the overall yields in the preparation of 30 and 31 were much lower than those obtained by applying the reactions of Scheme 6. Chemical equation presented.
68. Donohoe, T. J.; Moore, P. R.; Waring, M. J.; Newcombe, N. J. Tetrahedron Lett. 1997, 38, 5027.
69. Molyneux, R. J.; Pan, Y. T.; Tropea, J. E.; Benson, M.; Kaushal, G. P.: Elbein, A. D. Biochemistry 1901, 30, 9981.
70. Furneaux, R. H.; Gainsford, G. J.; Mason, J. M.; Tyler, P. C.; Hartley, O.; Winchester, B. G. Tetrahedron 1997, 53, 245.