Studies on the total synthesis of paraherquamide A. Stereocontrolled, asymmetric synthesis of α-alkyl-β-hydroxyproline derivatives

Tetrahedron Letters

Volumn 37, Issue 31, 1996, Pages 5441-5444

  Williams, Robert M ^a   Cao, Jianhua ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PARAHERQUAMIDE; PROLINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030605826     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01189-6     Document Type: Article

References (33)

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8. 3. (a) Omura, S.; Fujimoto, T.; Otoguro, K.; Matsuzaki, K.; Moriguchi, R., Tanaka, H.; Sasaki, Y., J. Antibiot. 1991, 44, 113;
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13. (f) Corey, E.J.; Reichard, G.A.; Kania, R., Tetrahedron Lett. 1993, 34, 6977;
14. (g) Sunazuka, T.; Nagamitsu, T.; Matsuzaki, K.; Tanaka, H.; Omura, S.; Smith, A.B., J.Am.Chem.Soc. 1993, 115, 5302.
15. 4. (a) Williams, R.M., Aldrichimica Acta 1992, 25, 11;
16. (b) Williams, R.M.; Im, M-N., J.Am.Chem.Soc. 1991, 113, 9276;
17. (c) Williams, R.M., Fegley, G.J., J.Am.Chem.Soc. 1991, 123, 8796;
18. (d) Williams, R.M., Advances in Asymmetric Synthesis, Hassner, A., Ed., JAI Press, 1995, Vol. 1, pp 45-94.
19. 5. (a) Cooper, J.; Gallagher, P.T.; Knight, D.W., J.Chem.Soc.Chem.Comm. 1988, 509;
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22. see also, (d) Sibi, M.P.; Christensen, J.W., Tetrahedron Lett. 1990, 31, 5689. Compound 5 was prepared as described in ref. 5b.
23. 6. (a) Gushing, T.D.; Sanz-Cervera, J.F.; Williams, R.M., J.Am.Chem.Soc. 1996, 118, 557; The absolute stereochemistry of the overall process was further corroborated by the conversion of 6a into the bicyclic substance 8 which (as the enantiomer) was previously converted into (+)-paraherquamide B, a substance whose absolute stereochemistry has been confirmed (see ref. 6a);
24. see also: (b) Williams, R.M.; Glinka, T.; Kwast, E.; Coffman, H.; Stille, J.K., J.Am.Chem.Soc. 1990, 112, 808: (equation presented)
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27. see also: (c) Dikshit, D.K.; Maheshwari, A.; Panday, S.K., Tetrahedron Lett. 1995, 36, 6131.
28. 8. Structure A was minimized and rendered on CSC Chem 3D Plus™.
29. 6Si: C, 60.36; H, 9.47; N, 3.06. Found: C, 60.17; H, 9.30; N, 3.05. (reaction scale: 1.67 g of 5).
30. 5: C, 62.36; H, 8.93; N, 4.28. Found: C, 62.19; H, 9.03; N, 4.27. (reaction scale: 312 mg of 5).
31. 5: C, 65.31; H, 7.79; N, 4.01. Found: C, 65.15; H, 7.69; N, 3.87. (reaction scale: 104 mg of 5).
32. 5: C, 57.13; H, 8.48; N, 5.12. Found: C, 56.92; H, 8.28; N, 5.05. (reaction scale: 104 mg of 5).
33. 5: C, 48.74; H, 7.16; N, 3.55. Found: C, 48.90; H, 7.31; N,3.60. (reaction scale: 104 mg of 5).