Stereocontrolled Synthesis of a Trihydroxylated Indolizidine Alkaloid, 1-Deoxycastanospermine

Synlett

Volumn 1997, Issue 8, 1997, Pages 911-912

  Yoda, Hidemi ^a   Nakajima, Tomohito ^a   Takabe, Kunihiko ^a  

^a SHIZUOKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002764933     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-962     Document Type: Article

References (18)

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3. Michael, J. P. Natural Products Reports 1990, 485.
4. (a) Humphries, M. J.; Matsumoto, K.; White, S. L.; Olden, K. Cancer Res. 1986, 46, 5215.
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7. (b) Fleet, G.W. J.; Karpas, A.; Dwek, R. A.; Fellows, L. E.; Tyms, A. S.; Petursson, S.; Namgoong, S. K.; Ramsden, N. G.; Smith, P. W.; Son, J. C.; Wilson, F.; Witty, D. R.; Jacob, G. S.; Rademacher, T. FEBS Lett. 1988, 237, 128.
8. For example: (a) Miller, S. A.; Chamberlin, A. R. J. Am. Chem. Soc. 1990, 112, 8100. (b) Gerspacher, M.; Rapoport, H. J. Org. Chem. 1991, 56, 3700. (c) Zhao, H.; Mootoo, D. R. J. Org. Chem. 1996, 61, 6762.
9. For example: (a) Miller, S. A.; Chamberlin, A. R. J. Am. Chem. Soc. 1990, 112, 8100. (b) Gerspacher, M.; Rapoport, H. J. Org. Chem. 1991, 56, 3700. (c) Zhao, H.; Mootoo, D. R. J. Org. Chem. 1996, 61, 6762.
10. For example: (a) Miller, S. A.; Chamberlin, A. R. J. Am. Chem. Soc. 1990, 112, 8100. (b) Gerspacher, M.; Rapoport, H. J. Org. Chem. 1991, 56, 3700. (c) Zhao, H.; Mootoo, D. R. J. Org. Chem. 1996, 61, 6762.
11. For example: (a) Hendry, D.; Hough, L.; Richardson, A. C. Tetrahedron 1988, 44, 6143. (b) Leeper, F. J.; Howard, S. Tetrahedron Lett. 1995, 36, 2335. (c) Martin, S. F.; Chen, H.-J.; Lynch, V. M. J. Org. Chem. 1995, 60, 276.
12. For example: (a) Hendry, D.; Hough, L.; Richardson, A. C. Tetrahedron 1988, 44, 6143. (b) Leeper, F. J.; Howard, S. Tetrahedron Lett. 1995, 36, 2335. (c) Martin, S. F.; Chen, H.-J.; Lynch, V. M. J. Org. Chem. 1995, 60, 276.
13. For example: (a) Hendry, D.; Hough, L.; Richardson, A. C. Tetrahedron 1988, 44, 6143. (b) Leeper, F. J.; Howard, S. Tetrahedron Lett. 1995, 36, 2335. (c) Martin, S. F.; Chen, H.-J.; Lynch, V. M. J. Org. Chem. 1995, 60, 276.
14. Yoda, H.; Kitayama, H.; Yamada, W.; Katagiri, T.; Takabe, K. Tetrahedron: Asymmetry 1993, 4, 1451. Yoda, H.; Kitayama, H.; Katagiri, T.; Takabe, K. Tetrahedron: Asymmetry 1993, 4, 1455.
15. Yoda, H.; Kitayama, H.; Yamada, W.; Katagiri, T.; Takabe, K. Tetrahedron: Asymmetry 1993, 4, 1451. Yoda, H.; Kitayama, H.; Katagiri, T.; Takabe, K. Tetrahedron: Asymmetry 1993, 4, 1455.
16. Yoda, H.; Yamazaki, H.; Kawauchi, M.; Takabe, K. Tetrahedron: Asymmetry 1995, 6, 2669.
17. Yoda, H.; Oguchi, T.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 2113.
18. Yoda, H.; Nakajima, T.; Takabe, K. Tetrahedron Lett. 1996, 37, 5531. After detailed investigations, the best result was observed under the conditions as shown in the text. The absolute configuration of the generated stereogenic center was assigned based on the spectral data of synthetic (+)-2 and triacetate (+)-13.