Diastereoselective isothiourea iodocyclization for manzacidin synthesis

Tetrahedron Letters

Volumn 44, Issue 14, 2003, Pages 2881-2883

  Woo, Jacqueline C S ^a   MacKay, D Bruce ^a  

^a MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; MANZACIDIN A; MANZACIDIN D; THIOUREA DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DIASTEREOISOMER; LOW TEMPERATURE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037474649     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00431-3     Document Type: Article

References (17)

1. For a recent two-part review of iodocyclization, see: (a) Frederickson, M.; Grigg, R. Org. Prep. Proc. Intl. 1997, 29, 33; (b) ibid, p. 63.
2. For a recent two-part review of iodocyclization, see: (a) Frederickson, M.; Grigg, R. Org. Prep. Proc. Intl. 1997, 29, 33; (b) ibid, p. 63.
3. Creeke P.I., Mellor J.M. Tetrahedron Lett. 30:1989;4435.
4. For examples of cyclizations of amidines mediated by: (a) acid, see: Partridge, M. A.; Smith, A. J. Chem. Soc., Perkin 1 1973, 453; (b) electrophilic halogen sources, see: (i) Hunt, P. A.; May, C.; Moody, C. J. Tetrahedron Lett. 1988, 29, 3001; (ii) Ershova, I. I.; Yu, I.; Staninets, V. I. Ukr. Khim. Zh. 1977, 43, 884; (iii) Chern, J.-W.; Shiau, C.-Y.; Lu, G.-Y. Bioorg. Med. Chem. Lett. 1991, 1, 571; (c) electrophilic selenium sources, see: Engman, L. J. Org. Chem. 1993, 58, 2394.
5. For examples of cyclizations of amidines mediated by: (a) acid, see: Partridge, M. A.; Smith, A. J. Chem. Soc., Perkin 1 1973, 453; (b) electrophilic halogen sources, see: (i) Hunt, P. A.; May, C.; Moody, C. J. Tetrahedron Lett. 1988, 29, 3001; (ii) Ershova, I. I.; Yu, I.; Staninets, V. I. Ukr. Khim. Zh. 1977, 43, 884; (iii) Chern, J.-W.; Shiau, C.-Y.; Lu, G.-Y. Bioorg. Med. Chem. Lett. 1991, 1, 571; (c) electrophilic selenium sources, see: Engman, L. J. Org. Chem. 1993, 58, 2394.
6. For examples of cyclizations of amidines mediated by: (a) acid, see: Partridge, M. A.; Smith, A. J. Chem. Soc., Perkin 1 1973, 453; (b) electrophilic halogen sources, see: (i) Hunt, P. A.; May, C.; Moody, C. J. Tetrahedron Lett. 1988, 29, 3001; (ii) Ershova, I. I.; Yu, I.; Staninets, V. I. Ukr. Khim. Zh. 1977, 43, 884; (iii) Chern, J.-W.; Shiau, C.-Y.; Lu, G.-Y. Bioorg. Med. Chem. Lett. 1991, 1, 571; (c) electrophilic selenium sources, see: Engman, L. J. Org. Chem. 1993, 58, 2394.
7. For examples of cyclizations of amidines mediated by: (a) acid, see: Partridge, M. A.; Smith, A. J. Chem. Soc., Perkin 1 1973, 453; (b) electrophilic halogen sources, see: (i) Hunt, P. A.; May, C.; Moody, C. J. Tetrahedron Lett. 1988, 29, 3001; (ii) Ershova, I. I.; Yu, I.; Staninets, V. I. Ukr. Khim. Zh. 1977, 43, 884; (iii) Chern, J.-W.; Shiau, C.-Y.; Lu, G.-Y. Bioorg. Med. Chem. Lett. 1991, 1, 571; (c) electrophilic selenium sources, see: Engman, L. J. Org. Chem. 1993, 58, 2394.
8. For examples of cyclizations of amidines mediated by: (a) acid, see: Partridge, M. A.; Smith, A. J. Chem. Soc., Perkin 1 1973, 453; (b) electrophilic halogen sources, see: (i) Hunt, P. A.; May, C.; Moody, C. J. Tetrahedron Lett. 1988, 29, 3001; (ii) Ershova, I. I.; Yu, I.; Staninets, V. I. Ukr. Khim. Zh. 1977, 43, 884; (iii) Chern, J.-W.; Shiau, C.-Y.; Lu, G.-Y. Bioorg. Med. Chem. Lett. 1991, 1, 571; (c) electrophilic selenium sources, see: Engman, L. J. Org. Chem. 1993, 58, 2394.
9. Kobayashi J., Kanda F., Ishibashi M., Shigemori H. J. Org. Chem. 56:1991;4574.
10. Jahn T., Konig G.M., Wright A.D. Tetrahedron Lett. 38:1997;3883.
11. Namba K., Shinada T., Teramoto T., Ohfune Y. J. Am. Chem. Soc. 122:2000;10708.
12. Wehn P.M., Du Bois J. J. Am. Chem. Soc. 124:2002;12950.
13. Note that this transformation can also be carried out enantioselectively using a chiral phase transfer catalyst, see: Ooi T., Kameda M., Maruoka K. J. Am. Chem. Soc. 121:1999;6519.
14. Moynihan H.A., Roberts S.M., Weldon H., Allcock G.H., Anggard E.E., Warner T.D. J. Chem. Soc., Perkin Trans. 1. 1994;769.
15. Esser F., Pook K.-H., Carpy A., Leger J.-M. Synthesis. 1994;77.
16. Takahata, H.; Takamatsu, T.; Yamazaki, T. J. Org. Chem. 1989, 54, 4812. See also: Takahata, H.; Takamatsu, T.; Chen, Y.-S.; Ohkubo, N.; Yamazaki, T.; Momose, T. J. Org. Chem. 1990, 55, 3792 and references cited therein.
17. Takahata, H.; Takamatsu, T.; Yamazaki, T. J. Org. Chem. 1989, 54, 4812. See also: Takahata, H.; Takamatsu, T.; Chen, Y.-S.; Ohkubo, N.; Yamazaki, T.; Momose, T. J. Org. Chem. 1990, 55, 3792 and references cited therein.