Synthesis of the angiotensin-converting enzyme inhibitors (-)-A58365A and (-)-A58365B from a common intermediate

Journal of Organic Chemistry

Volumn 64, Issue 5, 1999, Pages 1447-1454

  Clive, Derrick L J ^a   Coltart, Don M ^a   Zhou, Yuanxi ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

3 CARBOXY 1,2,3,5 TETRAHYDRO 8 HYDROXY 5 OXO 6 INDOLIZIDINEPROPIONIC ACID; 4 CARBOXY 1,3,4,6 TETRAHYDRO 9 HYDROXY 6 OXO 2H QUINOLIZINE 7 PROPIONIC ACID; ALDEHYDE DERIVATIVE; DIPEPTIDYL CARBOXYPEPTIDASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CYCLIZATION; DRUG SYNTHESIS; OXIDATION;

EID: 0033525833     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9822941     Document Type: Article

References (39)

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4. (b) Structure: Hunt, A. H.; Mynderse, J. S.; Samlaska, S. K.; Fukuda, D. S.; Maciak, G. M.; Kirst, H. A.; Occolowitz, J. L.; Swartzendruber, J. K.; Jones, N. D. J. Antibiot. 1988, 41, 771-779.
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11. For a synthesis of (±)-A58365B and formal syntheses of (±)-and (-)-A58365A, see: Wong, P. L.; Moeller, K. D. J. Am. Chem. Soc. 1993, 115, 11434-11445.
12. de Lima, D. P., Ph.D. Thesis, 1994, Universidade Federal Minas Gerais (Brazil). The studies on (±)-A58365B were done at the University of Alberta.
13. For example, treatment of 3 (n = 1, R = Me) with DDQ leads to i (see ref 6). Desaturation of 3 (n = 1 or 2, R = Me) had to be done in an indirect way (see ref 6). (Formula Presented)
14. Nonsystematic numbering.
15. For intermolecular addition of radicals (carrying electron-withdrawing groups) to the distal terminus of an enamine double bond, see: Renaud, P.; Schubert, S. Synlett 1990, 624-626. For intramolecular cyclization of a radical onto the proximal terminus of a enamide double bond, see: Yuasa, Y.; Kano, S.; Shibuya, S. Heterocycles 1991, 32, 2311-2314. Beckwith, A. L. J.; Joseph, S. P.; Mayadunne, R. T. A. J. Org. Chem. 1993, 58, 4198-4199. Beckwith, A. L. J.; Westwood, S. W. Tetrahedron 1989, 45, 5269-5282. For cyclization onto the distal terminus of an enamide double bond, see: Schultz, A. G.; Guzzo, P. R.; Nowak, D. M. J. Org. Chem. 1995, 60, 8044-8050.
16. For intermolecular addition of radicals (carrying electron-withdrawing groups) to the distal terminus of an enamine double bond, see: Renaud, P.; Schubert, S. Synlett 1990, 624-626. For intramolecular cyclization of a radical onto the proximal terminus of a enamide double bond, see: Yuasa, Y.; Kano, S.; Shibuya, S. Heterocycles 1991, 32, 2311-2314. Beckwith, A. L. J.; Joseph, S. P.; Mayadunne, R. T. A. J. Org. Chem. 1993, 58, 4198-4199. Beckwith, A. L. J.; Westwood, S. W. Tetrahedron 1989, 45, 5269-5282. For cyclization onto the distal terminus of an enamide double bond, see: Schultz, A. G.; Guzzo, P. R.; Nowak, D. M. J. Org. Chem. 1995, 60, 8044-8050.
17. For intermolecular addition of radicals (carrying electron-withdrawing groups) to the distal terminus of an enamine double bond, see: Renaud, P.; Schubert, S. Synlett 1990, 624-626. For intramolecular cyclization of a radical onto the proximal terminus of a enamide double bond, see: Yuasa, Y.; Kano, S.; Shibuya, S. Heterocycles 1991, 32, 2311-2314. Beckwith, A. L. J.; Joseph, S. P.; Mayadunne, R. T. A. J. Org. Chem. 1993, 58, 4198-4199. Beckwith, A. L. J.; Westwood, S. W. Tetrahedron 1989, 45, 5269-5282. For cyclization onto the distal terminus of an enamide double bond, see: Schultz, A. G.; Guzzo, P. R.; Nowak, D. M. J. Org. Chem. 1995, 60, 8044-8050.
18. For intermolecular addition of radicals (carrying electron-withdrawing groups) to the distal terminus of an enamine double bond, see: Renaud, P.; Schubert, S. Synlett 1990, 624-626. For intramolecular cyclization of a radical onto the proximal terminus of a enamide double bond, see: Yuasa, Y.; Kano, S.; Shibuya, S. Heterocycles 1991, 32, 2311-2314. Beckwith, A. L. J.; Joseph, S. P.; Mayadunne, R. T. A. J. Org. Chem. 1993, 58, 4198-4199. Beckwith, A. L. J.; Westwood, S. W. Tetrahedron 1989, 45, 5269-5282. For cyclization onto the distal terminus of an enamide double bond, see: Schultz, A. G.; Guzzo, P. R.; Nowak, D. M. J. Org. Chem. 1995, 60, 8044-8050.
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31. Cf. Paterson, I.; Cowden, C.; Watson, C. Synlett 1996, 209-211.
32. 2O).
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34. These exploratory studies were done on the more polar (TLC, silica gel) diastereoisomer [(+)-17b].
35. Cf. Brown, H. C.; Kulkarni, S. U.; Rao, C. G. Synthesis, 1980, 151-153.
36. Oxidation of the boranes to the aldehydes could also be done with TPAP, but in lower yield.
37. 2O).
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