Stereocontrolled sequential functionalization in acyclic systems by exploiting internal 1,2-asymmetric induction - Generation of symmetry-related polyamino alcohol motifs

Tetrahedron Letters

Volumn 37, Issue 42, 1996, Pages 7477-7480

  Hanessian, Stephen ^a   Wang, Wengui ^a   Gai, Yonghua ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030583508     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01754-6     Document Type: Article

References (39)

1. 1. In the area of renin inhibitors, see for example, Ocain, T.D.; Abou-Gharbia, M. Drugs of the Future 1991, 16, 37; Greenlee, W.J. Med. Chem. Rev. 1991, 16, 37; Greenlee, W.J. Med. Chem. Rev. 1990, 10, 173; Antonaccio, M.J.; Wright, J.J. Progr. Drug. Res. 1987, 31, 161; Plattner, J.J.; Leinert, H.D. Ann. Rep. Med. Chem. 1987, 22, 63; For HIV protease inhibitors, see Thaisrivongs, S. Chapter 14, Annu. Rep. Med. Chem. 1994, 29, 133; Darke, P.L.; Huff, J.R. Advances in Pharmacology; August, J.T.; Andres, M.W.; Murad, F. Eds.; Academic: San Diego 1994, vol. 25, 399; Wlodawer, A.; Erikson, J.W. Annu. Rev. Biochem. 1993, 62, 543; Clare, M. Perspect. Drug. Discovery Des. 1993, 1, 49; Lang, M.; Roesel, J. Arch. Pharm. (Weinheim, Ger.) 1993, 326, 921; Meek, T.D. J. Enzyme Inhib. 1992, 6, 65; Martin, J.A. Antiviral Res. 1992, 17, 265; Debouck, C. AIDS Res. Human Retroviruses 1992, 8(2), 153; Norbeck, D.W.; Kempf, D.J. Annu. Rep. Med. Chem. 1991, 26, 141; Tomasselli, A.G.; Howe, W.J.; Sawyer, T.K.; Wlodawer, A.; Heinrikson, R.L. Chim. Oggi. 1991, 9, 6; Huff, J.R. J. Med. Chem. 1991, 34, 2305.
2. 1. In the area of renin inhibitors, see for example, Ocain, T.D.; Abou-Gharbia, M. Drugs of the Future 1991, 16, 37; Greenlee, W.J. Med. Chem. Rev. 1991, 16, 37; Greenlee, W.J. Med. Chem. Rev. 1990, 10, 173; Antonaccio, M.J.; Wright, J.J. Progr. Drug. Res. 1987, 31, 161; Plattner, J.J.; Leinert, H.D. Ann. Rep. Med. Chem. 1987, 22, 63; For HIV protease inhibitors, see Thaisrivongs, S. Chapter 14, Annu. Rep. Med. Chem. 1994, 29, 133; Darke, P.L.; Huff, J.R. Advances in Pharmacology; August, J.T.; Andres, M.W.; Murad, F. Eds.; Academic: San Diego 1994, vol. 25, 399; Wlodawer, A.; Erikson, J.W. Annu. Rev. Biochem. 1993, 62, 543; Clare, M. Perspect. Drug. Discovery Des. 1993, 1, 49; Lang, M.; Roesel, J. Arch. Pharm. (Weinheim, Ger.) 1993, 326, 921; Meek, T.D. J. Enzyme Inhib. 1992, 6, 65; Martin, J.A. Antiviral Res. 1992, 17, 265; Debouck, C. AIDS Res. Human Retroviruses 1992, 8(2), 153; Norbeck, D.W.; Kempf, D.J. Annu. Rep. Med. Chem. 1991, 26, 141; Tomasselli, A.G.; Howe, W.J.; Sawyer, T.K.; Wlodawer, A.; Heinrikson, R.L. Chim. Oggi. 1991, 9, 6; Huff, J.R. J. Med. Chem. 1991, 34, 2305.
3. 1. In the area of renin inhibitors, see for example, Ocain, T.D.; Abou-Gharbia, M. Drugs of the Future 1991, 16, 37; Greenlee, W.J. Med. Chem. Rev. 1991, 16, 37; Greenlee, W.J. Med. Chem. Rev. 1990, 10, 173; Antonaccio, M.J.; Wright, J.J. Progr. Drug. Res. 1987, 31, 161; Plattner, J.J.; Leinert, H.D. Ann. Rep. Med. Chem. 1987, 22, 63; For HIV protease inhibitors, see Thaisrivongs, S. Chapter 14, Annu. Rep. Med. Chem. 1994, 29, 133; Darke, P.L.; Huff, J.R. Advances in Pharmacology; August, J.T.; Andres, M.W.; Murad, F. Eds.; Academic: San Diego 1994, vol. 25, 399; Wlodawer, A.; Erikson, J.W. Annu. Rev. Biochem. 1993, 62, 543; Clare, M. Perspect. Drug. Discovery Des. 1993, 1, 49; Lang, M.; Roesel, J. Arch. Pharm. (Weinheim, Ger.) 1993, 326, 921; Meek, T.D. J. Enzyme Inhib. 1992, 6, 65; Martin, J.A. Antiviral Res. 1992, 17, 265; Debouck, C. AIDS Res. Human Retroviruses 1992, 8(2), 153; Norbeck, D.W.; Kempf, D.J. Annu. Rep. Med. Chem. 1991, 26, 141; Tomasselli, A.G.; Howe, W.J.; Sawyer, T.K.; Wlodawer, A.; Heinrikson, R.L. Chim. Oggi. 1991, 9, 6; Huff, J.R. J. Med. Chem. 1991, 34, 2305.
4. 1. In the area of renin inhibitors, see for example, Ocain, T.D.; Abou-Gharbia, M. Drugs of the Future 1991, 16, 37; Greenlee, W.J. Med. Chem. Rev. 1991, 16, 37; Greenlee, W.J. Med. Chem. Rev. 1990, 10, 173; Antonaccio, M.J.; Wright, J.J. Progr. Drug. Res. 1987, 31, 161; Plattner, J.J.; Leinert, H.D. Ann. Rep. Med. Chem. 1987, 22, 63; For HIV protease inhibitors, see Thaisrivongs, S. Chapter 14, Annu. Rep. Med. Chem. 1994, 29, 133; Darke, P.L.; Huff, J.R. Advances in Pharmacology; August, J.T.; Andres, M.W.; Murad, F. Eds.; Academic: San Diego 1994, vol. 25, 399; Wlodawer, A.; Erikson, J.W. Annu. Rev. Biochem. 1993, 62, 543; Clare, M. Perspect. Drug. Discovery Des. 1993, 1, 49; Lang, M.; Roesel, J. Arch. Pharm. (Weinheim, Ger.) 1993, 326, 921; Meek, T.D. J. Enzyme Inhib. 1992, 6, 65; Martin, J.A. Antiviral Res. 1992, 17, 265; Debouck, C. AIDS Res. Human Retroviruses 1992, 8(2), 153; Norbeck, D.W.; Kempf, D.J. Annu. Rep. Med. Chem. 1991, 26, 141; Tomasselli, A.G.; Howe, W.J.; Sawyer, T.K.; Wlodawer, A.; Heinrikson, R.L. Chim. Oggi. 1991, 9, 6; Huff, J.R. J. Med. Chem. 1991, 34, 2305.
5. 1. In the area of renin inhibitors, see for example, Ocain, T.D.; Abou-Gharbia, M. Drugs of the Future 1991, 16, 37; Greenlee, W.J. Med. Chem. Rev. 1991, 16, 37; Greenlee, W.J. Med. Chem. Rev. 1990, 10, 173; Antonaccio, M.J.; Wright, J.J. Progr. Drug. Res. 1987, 31, 161; Plattner, J.J.; Leinert, H.D. Ann. Rep. Med. Chem. 1987, 22, 63; For HIV protease inhibitors, see Thaisrivongs, S. Chapter 14, Annu. Rep. Med. Chem. 1994, 29, 133; Darke, P.L.; Huff, J.R. Advances in Pharmacology; August, J.T.; Andres, M.W.; Murad, F. Eds.; Academic: San Diego 1994, vol. 25, 399; Wlodawer, A.; Erikson, J.W. Annu. Rev. Biochem. 1993, 62, 543; Clare, M. Perspect. Drug. Discovery Des. 1993, 1, 49; Lang, M.; Roesel, J. Arch. Pharm. (Weinheim, Ger.) 1993, 326, 921; Meek, T.D. J. Enzyme Inhib. 1992, 6, 65; Martin, J.A. Antiviral Res. 1992, 17, 265; Debouck, C. AIDS Res. Human Retroviruses 1992, 8(2), 153; Norbeck, D.W.; Kempf, D.J. Annu. Rep. Med. Chem. 1991, 26, 141; Tomasselli, A.G.; Howe, W.J.; Sawyer, T.K.; Wlodawer, A.; Heinrikson, R.L. Chim. Oggi. 1991, 9, 6; Huff, J.R. J. Med. Chem. 1991, 34, 2305.
6. 1. In the area of renin inhibitors, see for example, Ocain, T.D.; Abou-Gharbia, M. Drugs of the Future 1991, 16, 37; Greenlee, W.J. Med. Chem. Rev. 1991, 16, 37; Greenlee, W.J. Med. Chem. Rev. 1990, 10, 173; Antonaccio, M.J.; Wright, J.J. Progr. Drug. Res. 1987, 31, 161; Plattner, J.J.; Leinert, H.D. Ann. Rep. Med. Chem. 1987, 22, 63; For HIV protease inhibitors, see Thaisrivongs, S. Chapter 14, Annu. Rep. Med. Chem. 1994, 29, 133; Darke, P.L.; Huff, J.R. Advances in Pharmacology; August, J.T.; Andres, M.W.; Murad, F. Eds.; Academic: San Diego 1994, vol. 25, 399; Wlodawer, A.; Erikson, J.W. Annu. Rev. Biochem. 1993, 62, 543; Clare, M. Perspect. Drug. Discovery Des. 1993, 1, 49; Lang, M.; Roesel, J. Arch. Pharm. (Weinheim, Ger.) 1993, 326, 921; Meek, T.D. J. Enzyme Inhib. 1992, 6, 65; Martin, J.A. Antiviral Res. 1992, 17, 265; Debouck, C. AIDS Res. Human Retroviruses 1992, 8(2), 153; Norbeck, D.W.; Kempf, D.J. Annu. Rep. Med. Chem. 1991, 26, 141; Tomasselli, A.G.; Howe, W.J.; Sawyer, T.K.; Wlodawer, A.; Heinrikson, R.L. Chim. Oggi. 1991, 9, 6; Huff, J.R. J. Med. Chem. 1991, 34, 2305.
7. 1. In the area of renin inhibitors, see for example, Ocain, T.D.; Abou-Gharbia, M. Drugs of the Future 1991, 16, 37; Greenlee, W.J. Med. Chem. Rev. 1991, 16, 37; Greenlee, W.J. Med. Chem. Rev. 1990, 10, 173; Antonaccio, M.J.; Wright, J.J. Progr. Drug. Res. 1987, 31, 161; Plattner, J.J.; Leinert, H.D. Ann. Rep. Med. Chem. 1987, 22, 63; For HIV protease inhibitors, see Thaisrivongs, S. Chapter 14, Annu. Rep. Med. Chem. 1994, 29, 133; Darke, P.L.; Huff, J.R. Advances in Pharmacology; August, J.T.; Andres, M.W.; Murad, F. Eds.; Academic: San Diego 1994, vol. 25, 399; Wlodawer, A.; Erikson, J.W. Annu. Rev. Biochem. 1993, 62, 543; Clare, M. Perspect. Drug. Discovery Des. 1993, 1, 49; Lang, M.; Roesel, J. Arch. Pharm. (Weinheim, Ger.) 1993, 326, 921; Meek, T.D. J. Enzyme Inhib. 1992, 6, 65; Martin, J.A. Antiviral Res. 1992, 17, 265; Debouck, C. AIDS Res. Human Retroviruses 1992, 8(2), 153; Norbeck, D.W.; Kempf, D.J. Annu. Rep. Med. Chem. 1991, 26, 141; Tomasselli, A.G.; Howe, W.J.; Sawyer, T.K.; Wlodawer, A.; Heinrikson, R.L. Chim. Oggi. 1991, 9, 6; Huff, J.R. J. Med. Chem. 1991, 34, 2305.
8. 1. In the area of renin inhibitors, see for example, Ocain, T.D.; Abou-Gharbia, M. Drugs of the Future 1991, 16, 37; Greenlee, W.J. Med. Chem. Rev. 1991, 16, 37; Greenlee, W.J. Med. Chem. Rev. 1990, 10, 173; Antonaccio, M.J.; Wright, J.J. Progr. Drug. Res. 1987, 31, 161; Plattner, J.J.; Leinert, H.D. Ann. Rep. Med. Chem. 1987, 22, 63; For HIV protease inhibitors, see Thaisrivongs, S. Chapter 14, Annu. Rep. Med. Chem. 1994, 29, 133; Darke, P.L.; Huff, J.R. Advances in Pharmacology; August, J.T.; Andres, M.W.; Murad, F. Eds.; Academic: San Diego 1994, vol. 25, 399; Wlodawer, A.; Erikson, J.W. Annu. Rev. Biochem. 1993, 62, 543; Clare, M. Perspect. Drug. Discovery Des. 1993, 1, 49; Lang, M.; Roesel, J. Arch. Pharm. (Weinheim, Ger.) 1993, 326, 921; Meek, T.D. J. Enzyme Inhib. 1992, 6, 65; Martin, J.A. Antiviral Res. 1992, 17, 265; Debouck, C. AIDS Res. Human Retroviruses 1992, 8(2), 153; Norbeck, D.W.; Kempf, D.J. Annu. Rep. Med. Chem. 1991, 26, 141; Tomasselli, A.G.; Howe, W.J.; Sawyer, T.K.; Wlodawer, A.; Heinrikson, R.L. Chim. Oggi. 1991, 9, 6; Huff, J.R. J. Med. Chem. 1991, 34, 2305.
9. 1. In the area of renin inhibitors, see for example, Ocain, T.D.; Abou-Gharbia, M. Drugs of the Future 1991, 16, 37; Greenlee, W.J. Med. Chem. Rev. 1991, 16, 37; Greenlee, W.J. Med. Chem. Rev. 1990, 10, 173; Antonaccio, M.J.; Wright, J.J. Progr. Drug. Res. 1987, 31, 161; Plattner, J.J.; Leinert, H.D. Ann. Rep. Med. Chem. 1987, 22, 63; For HIV protease inhibitors, see Thaisrivongs, S. Chapter 14, Annu. Rep. Med. Chem. 1994, 29, 133; Darke, P.L.; Huff, J.R. Advances in Pharmacology; August, J.T.; Andres, M.W.; Murad, F. Eds.; Academic: San Diego 1994, vol. 25, 399; Wlodawer, A.; Erikson, J.W. Annu. Rev. Biochem. 1993, 62, 543; Clare, M. Perspect. Drug. Discovery Des. 1993, 1, 49; Lang, M.; Roesel, J. Arch. Pharm. (Weinheim, Ger.) 1993, 326, 921; Meek, T.D. J. Enzyme Inhib. 1992, 6, 65; Martin, J.A. Antiviral Res. 1992, 17, 265; Debouck, C. AIDS Res. Human Retroviruses 1992, 8(2), 153; Norbeck, D.W.; Kempf, D.J. Annu. Rep. Med. Chem. 1991, 26, 141; Tomasselli, A.G.; Howe, W.J.; Sawyer, T.K.; Wlodawer, A.; Heinrikson, R.L. Chim. Oggi. 1991, 9, 6; Huff, J.R. J. Med. Chem. 1991, 34, 2305.
10. 1. In the area of renin inhibitors, see for example, Ocain, T.D.; Abou-Gharbia, M. Drugs of the Future 1991, 16, 37; Greenlee, W.J. Med. Chem. Rev. 1991, 16, 37; Greenlee, W.J. Med. Chem. Rev. 1990, 10, 173; Antonaccio, M.J.; Wright, J.J. Progr. Drug. Res. 1987, 31, 161; Plattner, J.J.; Leinert, H.D. Ann. Rep. Med. Chem. 1987, 22, 63; For HIV protease inhibitors, see Thaisrivongs, S. Chapter 14, Annu. Rep. Med. Chem. 1994, 29, 133; Darke, P.L.; Huff, J.R. Advances in Pharmacology; August, J.T.; Andres, M.W.; Murad, F. Eds.; Academic: San Diego 1994, vol. 25, 399; Wlodawer, A.; Erikson, J.W. Annu. Rev. Biochem. 1993, 62, 543; Clare, M. Perspect. Drug. Discovery Des. 1993, 1, 49; Lang, M.; Roesel, J. Arch. Pharm. (Weinheim, Ger.) 1993, 326, 921; Meek, T.D. J. Enzyme Inhib. 1992, 6, 65; Martin, J.A. Antiviral Res. 1992, 17, 265; Debouck, C. AIDS Res. Human Retroviruses 1992, 8(2), 153; Norbeck, D.W.; Kempf, D.J. Annu. Rep. Med. Chem. 1991, 26, 141; Tomasselli, A.G.; Howe, W.J.; Sawyer, T.K.; Wlodawer, A.; Heinrikson, R.L. Chim. Oggi. 1991, 9, 6; Huff, J.R. J. Med. Chem. 1991, 34, 2305.
11. 1. In the area of renin inhibitors, see for example, Ocain, T.D.; Abou-Gharbia, M. Drugs of the Future 1991, 16, 37; Greenlee, W.J. Med. Chem. Rev. 1991, 16, 37; Greenlee, W.J. Med. Chem. Rev. 1990, 10, 173; Antonaccio, M.J.; Wright, J.J. Progr. Drug. Res. 1987, 31, 161; Plattner, J.J.; Leinert, H.D. Ann. Rep. Med. Chem. 1987, 22, 63; For HIV protease inhibitors, see Thaisrivongs, S. Chapter 14, Annu. Rep. Med. Chem. 1994, 29, 133; Darke, P.L.; Huff, J.R. Advances in Pharmacology; August, J.T.; Andres, M.W.; Murad, F. Eds.; Academic: San Diego 1994, vol. 25, 399; Wlodawer, A.; Erikson, J.W. Annu. Rev. Biochem. 1993, 62, 543; Clare, M. Perspect. Drug. Discovery Des. 1993, 1, 49; Lang, M.; Roesel, J. Arch. Pharm. (Weinheim, Ger.) 1993, 326, 921; Meek, T.D. J. Enzyme Inhib. 1992, 6, 65; Martin, J.A. Antiviral Res. 1992, 17, 265; Debouck, C. AIDS Res. Human Retroviruses 1992, 8(2), 153; Norbeck, D.W.; Kempf, D.J. Annu. Rep. Med. Chem. 1991, 26, 141; Tomasselli, A.G.; Howe, W.J.; Sawyer, T.K.; Wlodawer, A.; Heinrikson, R.L. Chim. Oggi. 1991, 9, 6; Huff, J.R. J. Med. Chem. 1991, 34, 2305.
12. 1. In the area of renin inhibitors, see for example, Ocain, T.D.; Abou-Gharbia, M. Drugs of the Future 1991, 16, 37; Greenlee, W.J. Med. Chem. Rev. 1991, 16, 37; Greenlee, W.J. Med. Chem. Rev. 1990, 10, 173; Antonaccio, M.J.; Wright, J.J. Progr. Drug. Res. 1987, 31, 161; Plattner, J.J.; Leinert, H.D. Ann. Rep. Med. Chem. 1987, 22, 63; For HIV protease inhibitors, see Thaisrivongs, S. Chapter 14, Annu. Rep. Med. Chem. 1994, 29, 133; Darke, P.L.; Huff, J.R. Advances in Pharmacology; August, J.T.; Andres, M.W.; Murad, F. Eds.; Academic: San Diego 1994, vol. 25, 399; Wlodawer, A.; Erikson, J.W. Annu. Rev. Biochem. 1993, 62, 543; Clare, M. Perspect. Drug. Discovery Des. 1993, 1, 49; Lang, M.; Roesel, J. Arch. Pharm. (Weinheim, Ger.) 1993, 326, 921; Meek, T.D. J. Enzyme Inhib. 1992, 6, 65; Martin, J.A. Antiviral Res. 1992, 17, 265; Debouck, C. AIDS Res. Human Retroviruses 1992, 8(2), 153; Norbeck, D.W.; Kempf, D.J. Annu. Rep. Med. Chem. 1991, 26, 141; Tomasselli, A.G.; Howe, W.J.; Sawyer, T.K.; Wlodawer, A.; Heinrikson, R.L. Chim. Oggi. 1991, 9, 6; Huff, J.R. J. Med. Chem. 1991, 34, 2305.
13. 1. In the area of renin inhibitors, see for example, Ocain, T.D.; Abou-Gharbia, M. Drugs of the Future 1991, 16, 37; Greenlee, W.J. Med. Chem. Rev. 1991, 16, 37; Greenlee, W.J. Med. Chem. Rev. 1990, 10, 173; Antonaccio, M.J.; Wright, J.J. Progr. Drug. Res. 1987, 31, 161; Plattner, J.J.; Leinert, H.D. Ann. Rep. Med. Chem. 1987, 22, 63; For HIV protease inhibitors, see Thaisrivongs, S. Chapter 14, Annu. Rep. Med. Chem. 1994, 29, 133; Darke, P.L.; Huff, J.R. Advances in Pharmacology; August, J.T.; Andres, M.W.; Murad, F. Eds.; Academic: San Diego 1994, vol. 25, 399; Wlodawer, A.; Erikson, J.W. Annu. Rev. Biochem. 1993, 62, 543; Clare, M. Perspect. Drug. Discovery Des. 1993, 1, 49; Lang, M.; Roesel, J. Arch. Pharm. (Weinheim, Ger.) 1993, 526, 921; Meek, T.D. J. Enzyme Inhib. 1992, 6, 65; Martin, J.A. Antiviral Res. 1992, 17, 265; Debouck, C. AIDS Res. Human Retroviruses 1992, 8(2), 153; Norbeck, D.W.; Kempf, D.J. Annu. Rep. Med. Chem. 1991, 26, 141; Tomasselli, A.G.; Howe, W.J.; Sawyer, T.K.; Wlodawer, A.; Heinrikson, R.L. Chim. Oggi. 1991, 9, 6; Huff, J.R. J. Med. Chem. 1991, 34, 2305.
14. 1. In the area of renin inhibitors, see for example, Ocain, T.D.; Abou-Gharbia, M. Drugs of the Future 1991, 16, 37; Greenlee, W.J. Med. Chem. Rev. 1991, 16, 37; Greenlee, W.J. Med. Chem. Rev. 1990, 10, 173; Antonaccio, M.J.; Wright, J.J. Progr. Drug. Res. 1987, 31, 161; Plattner, J.J.; Leinert, H.D. Ann. Rep. Med. Chem. 1987, 22, 63; For HIV protease inhibitors, see Thaisrivongs, S. Chapter 14, Annu. Rep. Med. Chem. 1994, 29, 133; Darke, P.L.; Huff, J.R. Advances in Pharmacology; August, J.T.; Andres, M.W.; Murad, F. Eds.; Academic: San Diego 1994, vol. 25, 399; Wlodawer, A.; Erikson, J.W. Annu. Rev. Biochem. 1993, 62, 543; Clare, M. Perspect. Drug. Discovery Des. 1993, 1, 49; Lang, M.; Roesel, J. Arch. Pharm. (Weinheim, Ger.) 1993, 526, 921; Meek, T.D. J. Enzyme Inhib. 1992, 6, 65; Martin, J.A. Antiviral Res. 1992, 17, 265; Debouck, C. AIDS Res. Human Retroviruses 1992, 8(2), 153; Norbeck, D.W.; Kempf, D.J. Annu. Rep. Med. Chem. 1991, 26, 141; Tomasselli, A.G.; Howe, W.J.; Sawyer, T.K.; Wlodawer, A.; Heinrikson, R.L. Chim. Oggi. 1991, 9, 6; Huff, J.R. J. Med. Chem. 1991, 34, 2305.
15. 1. In the area of renin inhibitors, see for example, Ocain, T.D.; Abou-Gharbia, M. Drugs of the Future 1991, 16, 37; Greenlee, W.J. Med. Chem. Rev. 1991, 16, 37; Greenlee, W.J. Med. Chem. Rev. 1990, 10, 173; Antonaccio, M.J.; Wright, J.J. Progr. Drug. Res. 1987, 31, 161; Plattner, J.J.; Leinert, H.D. Ann. Rep. Med. Chem. 1987, 22, 63; For HIV protease inhibitors, see Thaisrivongs, S. Chapter 14, Annu. Rep. Med. Chem. 1994, 29, 133; Darke, P.L.; Huff, J.R. Advances in Pharmacology; August, J.T.; Andres, M.W.; Murad, F. Eds.; Academic: San Diego 1994, vol. 25, 399; Wlodawer, A.; Erikson, J.W. Annu. Rev. Biochem. 1993, 62, 543; Clare, M. Perspect. Drug. Discovery Des. 1993, 1, 49; Lang, M.; Roesel, J. Arch. Pharm. (Weinheim, Ger.) 1993, 526, 921; Meek, T.D. J. Enzyme Inhib. 1992, 6, 65; Martin, J.A. Antiviral Res. 1992, 17, 265; Debouck, C. AIDS Res. Human Retroviruses 1992, 8(2), 153; Norbeck, D.W.; Kempf, D.J. Annu. Rep. Med. Chem. 1991, 26, 141; Tomasselli, A.G.; Howe, W.J.; Sawyer, T.K.; Wlodawer, A.; Heinrikson, R.L. Chim. Oggi. 1991, 9, 6; Huff, J.R. J. Med. Chem. 1991, 34, 2305.
16. 1. In the area of renin inhibitors, see for example, Ocain, T.D.; Abou-Gharbia, M. Drugs of the Future 1991, 16, 37; Greenlee, W.J. Med. Chem. Rev. 1991, 16, 37; Greenlee, W.J. Med. Chem. Rev. 1990, 10, 173; Antonaccio, M.J.; Wright, J.J. Progr. Drug. Res. 1987, 31, 161; Plattner, J.J.; Leinert, H.D. Ann. Rep. Med. Chem. 1987, 22, 63; For HIV protease inhibitors, see Thaisrivongs, S. Chapter 14, Annu. Rep. Med. Chem. 1994, 29, 133; Darke, P.L.; Huff, J.R. Advances in Pharmacology; August, J.T.; Andres, M.W.; Murad, F. Eds.; Academic: San Diego 1994, vol. 25, 399; Wlodawer, A.; Erikson, J.W. Annu. Rev. Biochem. 1993, 62, 543; Clare, M. Perspect. Drug. Discovery Des. 1993, 1, 49; Lang, M.; Roesel, J. Arch. Pharm. (Weinheim, Ger.) 1993, 326, 921; Meek, T.D. J. Enzyme Inhib. 1992, 6, 65; Martin, J.A. Antiviral Res. 1992, 17, 265; Debouck, C. AIDS Res. Human Retroviruses 1992, 8(2), 153; Norbeck, D.W.; Kempf, D.J. Annu. Rep. Med. Chem. 1991, 26, 141; Tomasselli, A.G.; Howe, W.J.; Sawyer, T.K.; Wlodawer, A.; Heinrikson, R.L. Chim. Oggi. 1991, 9, 6; Huff, J.R. J. Med. Chem. 1991, 34, 2305.
17. 2. For recent reviews, see Duthaler, R.O. Tetrahedron 1994, 50, 1539; Williams, R.M. Synthesis of Optically Active α-Amino Acids, Pergamon Press 1989, New York, N.Y.
18. 2. For recent reviews, see Duthaler, R.O. Tetrahedron 1994, 50, 1539; Williams, R.M. Synthesis of Optically Active α-Amino Acids, Pergamon Press 1989, New York, N.Y.
19. 3. For excellent recent reviews, see a. Thompson, L.A.; Ellman, J.A. Chem. Rev. 1996, 96, 555; b. Terrett, N.K.; Gardner, M.; Gordon, D.W.; Kobylecki, R.J.; Steele, J. Tetrahedron 1995, 51, 8135; c. Lowe, G. Chem. Soc. Rev. 1995, 309.
20. 3. For excellent recent reviews, see a. Thompson, L.A.; Ellman, J.A. Chem. Rev. 1996, 96, 555; b. Terrett, N.K.; Gardner, M.; Gordon, D.W.; Kobylecki, R.J.; Steele, J. Tetrahedron 1995, 51, 8135; c. Lowe, G. Chem. Soc. Rev. 1995, 309.
21. 3. For excellent recent reviews, see a. Thompson, L.A.; Ellman, J.A. Chem. Rev. 1996, 96, 555; b. Terrett, N.K.; Gardner, M.; Gordon, D.W.; Kobylecki, R.J.; Steele, J. Tetrahedron 1995, 51, 8135; c. Lowe, G. Chem. Soc. Rev. 1995, 309.
22. 4. Hanessian, S.; Gai, Y.; Wang, W. preceding paper.
23. 5. Hanessian, S.; Sumi, K. Synthesis 1991, 1083 and references cited therein.
24. 6. For examples see, a. Reetz, M.J.; Röhrig, D. Angew. Chem. Int. Ed. Engl. 1989, 28, 1706;
25. b. Iako, I.; Uiber, P.; Mann, A.; Taddei, M.; Wermuth, C.-G. Tetrahedron Lett. 1990, 31, 1011;
26. c. Cardani, S. Poli, G.; Scolastico, C.; Villa, R. Tetrahedron 1988, 44, 5929.
27. 7. Evans, D.A.; Britton, I.C. J. Am. Chem. Soc. 1987, 109, 6881; Evans, D.A.; Ellman, J.A.; J. Am. Chem. Soc. 1989, 111, 1063; Wasserman, H.H.; Hlasta, D.J. J. Am. Chem. Soc. 1978, 100, 6780; Wasserman, H.H.; Hlasta, D.J.; Tremper, A.W.; Wu, J.S. J. Org. Chem. 1981, 46, 2999; Kühlein, K.; Jensen, H. Justus Liebigs Ann., Chem. 1974, 369; see also Nishida, A.; Shibasaki, M.; Ikegami, S. Tetrahedron Lett. 1984, 25, 765; Shibuya, M.; Jonbo, Y., Kubota, S. Chem. Pharm. Bull., 1984, 32, 1303.
28. 7. Evans, D.A.; Britton, I.C. J. Am. Chem. Soc. 1987, 109, 6881; Evans, D.A.; Ellman, J.A.; J. Am. Chem. Soc. 1989, 111, 1063; Wasserman, H.H.; Hlasta, D.J. J. Am. Chem. Soc. 1978, 100, 6780; Wasserman, H.H.; Hlasta, D.J.; Tremper, A.W.; Wu, J.S. J. Org. Chem. 1981, 46, 2999; Kühlein, K.; Jensen, H. Justus Liebigs Ann., Chem. 1974, 369; see also Nishida, A.; Shibasaki, M.; Ikegami, S. Tetrahedron Lett. 1984, 25, 765; Shibuya, M.; Jonbo, Y., Kubota, S. Chem. Pharm. Bull., 1984, 32, 1303.
29. 7. Evans, D.A.; Britton, I.C. J. Am. Chem. Soc. 1987, 109, 6881; Evans, D.A.; Ellman, J.A.; J. Am. Chem. Soc. 1989, 111, 1063; Wasserman, H.H.; Hlasta, D.J. J. Am. Chem. Soc. 1978, 100, 6780; Wasserman, H.H.; Hlasta, D.J.; Tremper, A.W.; Wu, J.S. J. Org. Chem. 1981, 46, 2999; Kühlein, K.; Jensen, H. Justus Liebigs Ann., Chem. 1974, 369; see also Nishida, A.; Shibasaki, M.; Ikegami, S. Tetrahedron Lett. 1984, 25, 765; Shibuya, M.; Jonbo, Y., Kubota, S. Chem. Pharm. Bull., 1984, 32, 1303.
30. 7. Evans, D.A.; Britton, I.C. J. Am. Chem. Soc. 1987, 109, 6881; Evans, D.A.; Ellman, J.A.; J. Am. Chem. Soc. 1989, 111, 1063; Wasserman, H.H.; Hlasta, D.J. J. Am. Chem. Soc. 1978, 100, 6780; Wasserman, H.H.; Hlasta, D.J.; Tremper, A.W.; Wu, J.S. J. Org. Chem. 1981, 46, 2999; Kühlein, K.; Jensen, H. Justus Liebigs Ann., Chem. 1974, 369; see also Nishida, A.; Shibasaki, M.; Ikegami, S. Tetrahedron Lett. 1984, 25, 765; Shibuya, M.; Jonbo, Y., Kubota, S. Chem. Pharm. Bull., 1984, 32, 1303.
31. 7. Evans, D.A.; Britton, I.C. J. Am. Chem. Soc. 1987, 109, 6881; Evans, D.A.; Ellman, J.A.; J. Am. Chem. Soc. 1989, 111, 1063; Wasserman, H.H.; Hlasta, D.J. J. Am. Chem. Soc. 1978, 100, 6780; Wasserman, H.H.; Hlasta, D.J.; Tremper, A.W.; Wu, J.S. J. Org. Chem. 1981, 46, 2999; Kühlein, K.; Jensen, H. Justus Liebigs Ann., Chem. 1974, 369; see also Nishida, A.; Shibasaki, M.; Ikegami, S. Tetrahedron Lett. 1984, 25, 765; Shibuya, M.; Jonbo, Y., Kubota, S. Chem. Pharm. Bull., 1984, 32, 1303.
32. 7. Evans, D.A.; Britton, I.C. J. Am. Chem. Soc. 1987, 109, 6881; Evans, D.A.; Ellman, J.A.; J. Am. Chem. Soc. 1989, 111, 1063; Wasserman, H.H.; Hlasta, D.J. J. Am. Chem. Soc. 1978, 100, 6780; Wasserman, H.H.; Hlasta, D.J.; Tremper, A.W.; Wu, J.S. J. Org. Chem. 1981, 46, 2999; Kühlein, K.; Jensen, H. Justus Liebigs Ann., Chem. 1974, 369; see also Nishida, A.; Shibasaki, M.; Ikegami, S. Tetrahedron Lett. 1984, 25, 765; Shibuya, M.; Jonbo, Y., Kubota, S. Chem. Pharm. Bull., 1984, 32, 1303.
33. 7. Evans, D.A.; Britton, I.C. J. Am. Chem. Soc. 1987, 109, 6881; Evans, D.A.; Ellman, J.A.; J. Am. Chem. Soc. 1989, 111, 1063; Wasserman, H.H.; Hlasta, D.J. J. Am. Chem. Soc. 1978, 100, 6780; Wasserman, H.H.; Hlasta, D.J.; Tremper, A.W.; Wu, J.S. J. Org. Chem. 1981, 46, 2999; Kühlein, K.; Jensen, H. Justus Liebigs Ann., Chem. 1974, 369; see also Nishida, A.; Shibasaki, M.; Ikegami, S. Tetrahedron Lett. 1984, 25, 765; Shibuya, M.; Jonbo, Y., Kubota, S. Chem. Pharm. Bull., 1984, 32, 1303.
34. 4. The product was purified by flash chromatography.
35. 9. Vishwarkarma, L.C.; Slunger, O.D.; Davis, F.A. Org. Syn. 1986, 66, 203.
36. 10. Mitsunobu, O. Synthesis 1981, 1.
37. 11. For an example of enolate hydroxytation of an α-aminoketone derivative (1,3-induction); see Alexander, C.W.; Liotta, D.C. Tetrahedron Lett., 1996, 37, 1961.
38. 12. See for example Enders, D.; Jegelka, U.; Dücker, B. Angew. Chem. Int. Ed. Engl., 1993, 32, 423; Palono, C.; Aizpurua, J.M.; Urchegui, R.; Garciá, J.M. J. Org. Chem., 1993, 58, 1646; and references cited therein.
39. 12. See for example Enders, D.; Jegelka, U.; Dücker, B. Angew. Chem. Int. Ed. Engl., 1993, 32, 423; Palono, C.; Aizpurua, J.M.; Urchegui, R.; Garciá, J.M. J. Org. Chem., 1993, 58, 1646; and references cited therein.