Stereocontrolled Construction of the A-Ring of Nitiol Using a Pauson-Khand Cycloaddition-Ring Fragmentation Strategy

Organic Letters

Volumn 3, Issue 13, 2001, Pages 2041-2044

  Wilson, Michael S ^a   Dake, Gregory R ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

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EID: 0042839671     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016002l     Document Type: Article

References (25)

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14. All new compounds have been satisfactorily characterized spectroscopically (NMR, IR, MS).
15. For an enantioselective construction of the A-ring, pig liver esterase could be used to desymmetrize malonates 11 or 12. As the remainder of the construction is stereoselective, this step would define the absolute stereochemistry for the construction of the western half of 1. Trost, B. M.; Li, Y. J. Am. Chem. Soc. 1996, 118, 6625. Björkling, F.; Boutelje, J.; Gatenbeck, S.; Hult, K.; Norin, T.; Szmulik, T. Tetrahedron 1985, 41, 1347. Luyten, M.; Müller, S.; Herzog, B.; Keese, R. Helv. Chim. Acta 1987, 70, 1250. Toone. E. J.; Jones, J. B. Tetrahedron: Asymmetry 1991, 2, 1041.
16. For an enantioselective construction of the A-ring, pig liver esterase could be used to desymmetrize malonates 11 or 12. As the remainder of the construction is stereoselective, this step would define the absolute stereochemistry for the construction of the western half of 1. Trost, B. M.; Li, Y. J. Am. Chem. Soc. 1996, 118, 6625. Björkling, F.; Boutelje, J.; Gatenbeck, S.; Hult, K.; Norin, T.; Szmulik, T. Tetrahedron 1985, 41, 1347. Luyten, M.; Müller, S.; Herzog, B.; Keese, R. Helv. Chim. Acta 1987, 70, 1250. Toone. E. J.; Jones, J. B. Tetrahedron: Asymmetry 1991, 2, 1041.
17. For an enantioselective construction of the A-ring, pig liver esterase could be used to desymmetrize malonates 11 or 12. As the remainder of the construction is stereoselective, this step would define the absolute stereochemistry for the construction of the western half of 1. Trost, B. M.; Li, Y. J. Am. Chem. Soc. 1996, 118, 6625. Björkling, F.; Boutelje, J.; Gatenbeck, S.; Hult, K.; Norin, T.; Szmulik, T. Tetrahedron 1985, 41, 1347. Luyten, M.; Müller, S.; Herzog, B.; Keese, R. Helv. Chim. Acta 1987, 70, 1250. Toone. E. J.; Jones, J. B. Tetrahedron: Asymmetry 1991, 2, 1041.
18. For an enantioselective construction of the A-ring, pig liver esterase could be used to desymmetrize malonates 11 or 12. As the remainder of the construction is stereoselective, this step would define the absolute stereochemistry for the construction of the western half of 1. Trost, B. M.; Li, Y. J. Am. Chem. Soc. 1996, 118, 6625. Björkling, F.; Boutelje, J.; Gatenbeck, S.; Hult, K.; Norin, T.; Szmulik, T. Tetrahedron 1985, 41, 1347. Luyten, M.; Müller, S.; Herzog, B.; Keese, R. Helv. Chim. Acta 1987, 70, 1250. Toone. E. J.; Jones, J. B. Tetrahedron: Asymmetry 1991, 2, 1041.
19. (a) No promoter: Exon, C.; Magnus, P. J. Am. Chem. Soc. 1983, 105, 2477.
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21. 5SMe: Sugihara, T.; Yamada, M.; Yamaguchi, M.; Nishizawa, M. Synlett 1999, 771.
22. (d) DMSO: Chung, Y. K.; Lee, B. Y.; Jeong, N.; Hudecek, M.; Pauson, P. L. Organometallics 1993, 12, 220.
23. 4OH: Sugihara, T.; Yamada, M.; Yamaguchi, M.; Kaneko, C. Angew. Chem., Iny. Ef. Engl. 1997, 36, 2601.
24. (f) Krafft, M. E.; Bonaga, L. V. R.; Hirosawa, C. J. Org. Chem. 2001, 66, 3004.
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