Enantio- and diastereoselective synthesis of N-[(1R,2R,3R,4R)-2,3- diacetoxy-4-(acetoxymethyl)cyclopentyl]acetamide, a synthetic key intermediate of (+)-cyclaradine

Chemical and Pharmaceutical Bulletin

Volumn 46, Issue 5, 1998, Pages 842-845

  Norimine, Yoshihiko ^a   Hayashi, Masaki ^a   Tanaka, Masakazu ^a   Suemune, Hiroshi ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

(+) cyclaradine; Enantio and diastereoselective synthesis; Enantiomerically pure form

Indexed keywords

CARBOCYCLIC NUCLEOSIDE; CYCLARADINE; FUNCTIONAL GROUP; N [2,3 DIACETOXY 4 (ACETOXYMETHYL)CYCLOPENTYL]ACETAMIDE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; HYDROLYSIS; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0031835122     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.46.842     Document Type: Article

References (22)

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6. b) Katagiri N., Matsuhashi Y., Kokufuda H., Takebayashi M., Kaneko C., Tetrahedron Lett., 38, 1961-1964 (1997); Yoshikawa M., Murakami N., Inoue Y., Hatakeyama S., Kitagawa I., Chem. Pharm. Bull., 41, 636-638 (1993); Vince R., Brownell J., Daluge S., J. Med. Chem., 27, 1358-1360 (1984); Vince R., Daluge S., ibid., 20, 612-613 (1977); Vince R., Daluge S., Lee H., Shannon W. M., Arnett G., Schafer T. W., Nagabusham T. L., Reichert P., Tsai H., Science, 221, 1405-1406 (1983).
7. Bianco A., Mazzei R. A., Tetrahedron Lett., 38, 6433-6436 (1997); Zhang D. Y., Ghosh A., Suling C., Miller M. J., ibid., 37, 3799-3802 (1996); Jeong L. S., Marquez V. E., ibid., 37, 2353-2356 (1996); Tanaka M., Norimine Y., Fujita T., Suemune H., Sakai K., J. Org. Chem., 61, 6952-6957 (1996); Boyer S. J., Leahy J. W., ibid., 62, 3976-3980 (1997); Martins L. E., Nugent W. A., Jacobsen E. N., ibid., 61, 7963-7966 (1996); Deardorff D. R., Savin K. A., Justman C. J., Karanjawala Z. E., Sheppeck J. E., Hager D. C., Aydin N., ibid., 61, 3616-3622 (1996); Leeruff E., Xi F. D., Qie J. H., ibid., 61, 1547-1550 (1996); Altmann H., Kesselring R., Pieles U., Tetrahedron., 52, 12699-12722 (1996); Obara T., Shuto S., Saito Y., Snkeck R., Andrei G., Balzarini J., Deckercq E., Matsuda A., J. Med. Chem., 39, 3847-3852 (1996); Theil F., Ballschuh S., Vonjantalipinski M., Johnson R. A., J. Chem. Soc. Perkin Trans. 1, 1996, 255-258; Biadatti T., Esker J. L., Johnson C. R., Tetrahedron Asymmetry, 7, 2313-2320 (1996), and other references cited therein.
8. Bianco A., Mazzei R. A., Tetrahedron Lett., 38, 6433-6436 (1997); Zhang D. Y., Ghosh A., Suling C., Miller M. J., ibid., 37, 3799-3802 (1996); Jeong L. S., Marquez V. E., ibid., 37, 2353-2356 (1996); Tanaka M., Norimine Y., Fujita T., Suemune H., Sakai K., J. Org. Chem., 61, 6952-6957 (1996); Boyer S. J., Leahy J. W., ibid., 62, 3976-3980 (1997); Martins L. E., Nugent W. A., Jacobsen E. N., ibid., 61, 7963-7966 (1996); Deardorff D. R., Savin K. A., Justman C. J., Karanjawala Z. E., Sheppeck J. E., Hager D. C., Aydin N., ibid., 61, 3616-3622 (1996); Leeruff E., Xi F. D., Qie J. H., ibid., 61, 1547-1550 (1996); Altmann H., Kesselring R., Pieles U., Tetrahedron., 52, 12699-12722 (1996); Obara T., Shuto S., Saito Y., Snkeck R., Andrei G., Balzarini J., Deckercq E., Matsuda A., J. Med. Chem., 39, 3847-3852 (1996); Theil F., Ballschuh S., Vonjantalipinski M., Johnson R. A., J. Chem. Soc. Perkin Trans. 1, 1996, 255-258; Biadatti T., Esker J. L., Johnson C. R., Tetrahedron Asymmetry, 7, 2313-2320 (1996), and other references cited therein.
9. Bianco A., Mazzei R. A., Tetrahedron Lett., 38, 6433-6436 (1997); Zhang D. Y., Ghosh A., Suling C., Miller M. J., ibid., 37, 3799-3802 (1996); Jeong L. S., Marquez V. E., ibid., 37, 2353-2356 (1996); Tanaka M., Norimine Y., Fujita T., Suemune H., Sakai K., J. Org. Chem., 61, 6952-6957 (1996); Boyer S. J., Leahy J. W., ibid., 62, 3976-3980 (1997); Martins L. E., Nugent W. A., Jacobsen E. N., ibid., 61, 7963-7966 (1996); Deardorff D. R., Savin K. A., Justman C. J., Karanjawala Z. E., Sheppeck J. E., Hager D. C., Aydin N., ibid., 61, 3616-3622 (1996); Leeruff E., Xi F. D., Qie J. H., ibid., 61, 1547-1550 (1996); Altmann H., Kesselring R., Pieles U., Tetrahedron., 52, 12699-12722 (1996); Obara T., Shuto S., Saito Y., Snkeck R., Andrei G., Balzarini J., Deckercq E., Matsuda A., J. Med. Chem., 39, 3847-3852 (1996); Theil F., Ballschuh S., Vonjantalipinski M., Johnson R. A., J. Chem. Soc. Perkin Trans. 1, 1996, 255-258; Biadatti T., Esker J. L., Johnson C. R., Tetrahedron Asymmetry, 7, 2313-2320 (1996), and other references cited therein.
10. Bianco A., Mazzei R. A., Tetrahedron Lett., 38, 6433-6436 (1997); Zhang D. Y., Ghosh A., Suling C., Miller M. J., ibid., 37, 3799-3802 (1996); Jeong L. S., Marquez V. E., ibid., 37, 2353-2356 (1996); Tanaka M., Norimine Y., Fujita T., Suemune H., Sakai K., J. Org. Chem., 61, 6952-6957 (1996); Boyer S. J., Leahy J. W., ibid., 62, 3976-3980 (1997); Martins L. E., Nugent W. A., Jacobsen E. N., ibid., 61, 7963-7966 (1996); Deardorff D. R., Savin K. A., Justman C. J., Karanjawala Z. E., Sheppeck J. E., Hager D. C., Aydin N., ibid., 61, 3616-3622 (1996); Leeruff E., Xi F. D., Qie J. H., ibid., 61, 1547-1550 (1996); Altmann H., Kesselring R., Pieles U., Tetrahedron., 52, 12699-12722 (1996); Obara T., Shuto S., Saito Y., Snkeck R., Andrei G., Balzarini J., Deckercq E., Matsuda A., J. Med. Chem., 39, 3847-3852 (1996); Theil F., Ballschuh S., Vonjantalipinski M., Johnson R. A., J. Chem. Soc. Perkin Trans. 1, 1996, 255-258; Biadatti T., Esker J. L., Johnson C. R., Tetrahedron Asymmetry, 7, 2313-2320 (1996), and other references cited therein.
11. Bianco A., Mazzei R. A., Tetrahedron Lett., 38, 6433-6436 (1997); Zhang D. Y., Ghosh A., Suling C., Miller M. J., ibid., 37, 3799-3802 (1996); Jeong L. S., Marquez V. E., ibid., 37, 2353-2356 (1996); Tanaka M., Norimine Y., Fujita T., Suemune H., Sakai K., J. Org. Chem., 61, 6952-6957 (1996); Boyer S. J., Leahy J. W., ibid., 62, 3976-3980 (1997); Martins L. E., Nugent W. A., Jacobsen E. N., ibid., 61, 7963-7966 (1996); Deardorff D. R., Savin K. A., Justman C. J., Karanjawala Z. E., Sheppeck J. E., Hager D. C., Aydin N., ibid., 61, 3616-3622 (1996); Leeruff E., Xi F. D., Qie J. H., ibid., 61, 1547-1550 (1996); Altmann H., Kesselring R., Pieles U., Tetrahedron., 52, 12699-12722 (1996); Obara T., Shuto S., Saito Y., Snkeck R., Andrei G., Balzarini J., Deckercq E., Matsuda A., J. Med. Chem., 39, 3847-3852 (1996); Theil F., Ballschuh S., Vonjantalipinski M., Johnson R. A., J. Chem. Soc. Perkin Trans. 1, 1996, 255-258; Biadatti T., Esker J. L., Johnson C. R., Tetrahedron Asymmetry, 7, 2313-2320 (1996), and other references cited therein.
12. Bianco A., Mazzei R. A., Tetrahedron Lett., 38, 6433-6436 (1997); Zhang D. Y., Ghosh A., Suling C., Miller M. J., ibid., 37, 3799-3802 (1996); Jeong L. S., Marquez V. E., ibid., 37, 2353-2356 (1996); Tanaka M., Norimine Y., Fujita T., Suemune H., Sakai K., J. Org. Chem., 61, 6952-6957 (1996); Boyer S. J., Leahy J. W., ibid., 62, 3976-3980 (1997); Martins L. E., Nugent W. A., Jacobsen E. N., ibid., 61, 7963-7966 (1996); Deardorff D. R., Savin K. A., Justman C. J., Karanjawala Z. E., Sheppeck J. E., Hager D. C., Aydin N., ibid., 61, 3616-3622 (1996); Leeruff E., Xi F. D., Qie J. H., ibid., 61, 1547-1550 (1996); Altmann H., Kesselring R., Pieles U., Tetrahedron., 52, 12699-12722 (1996); Obara T., Shuto S., Saito Y., Snkeck R., Andrei G., Balzarini J., Deckercq E., Matsuda A., J. Med. Chem., 39, 3847-3852 (1996); Theil F., Ballschuh S., Vonjantalipinski M., Johnson R. A., J. Chem. Soc. Perkin Trans. 1, 1996, 255-258; Biadatti T., Esker J. L., Johnson C. R., Tetrahedron Asymmetry, 7, 2313-2320 (1996), and other references cited therein.
13. Bianco A., Mazzei R. A., Tetrahedron Lett., 38, 6433-6436 (1997); Zhang D. Y., Ghosh A., Suling C., Miller M. J., ibid., 37, 3799-3802 (1996); Jeong L. S., Marquez V. E., ibid., 37, 2353-2356 (1996); Tanaka M., Norimine Y., Fujita T., Suemune H., Sakai K., J. Org. Chem., 61, 6952-6957 (1996); Boyer S. J., Leahy J. W., ibid., 62, 3976-3980 (1997); Martins L. E., Nugent W. A., Jacobsen E. N., ibid., 61, 7963-7966 (1996); Deardorff D. R., Savin K. A., Justman C. J., Karanjawala Z. E., Sheppeck J. E., Hager D. C., Aydin N., ibid., 61, 3616-3622 (1996); Leeruff E., Xi F. D., Qie J. H., ibid., 61, 1547-1550 (1996); Altmann H., Kesselring R., Pieles U., Tetrahedron., 52, 12699-12722 (1996); Obara T., Shuto S., Saito Y., Snkeck R., Andrei G., Balzarini J., Deckercq E., Matsuda A., J. Med. Chem., 39, 3847-3852 (1996); Theil F., Ballschuh S., Vonjantalipinski M., Johnson R. A., J. Chem. Soc. Perkin Trans. 1, 1996, 255-258; Biadatti T., Esker J. L., Johnson C. R., Tetrahedron Asymmetry, 7, 2313-2320 (1996), and other references cited therein.
14. Bianco A., Mazzei R. A., Tetrahedron Lett., 38, 6433-6436 (1997); Zhang D. Y., Ghosh A., Suling C., Miller M. J., ibid., 37, 3799-3802 (1996); Jeong L. S., Marquez V. E., ibid., 37, 2353-2356 (1996); Tanaka M., Norimine Y., Fujita T., Suemune H., Sakai K., J. Org. Chem., 61, 6952-6957 (1996); Boyer S. J., Leahy J. W., ibid., 62, 3976-3980 (1997); Martins L. E., Nugent W. A., Jacobsen E. N., ibid., 61, 7963-7966 (1996); Deardorff D. R., Savin K. A., Justman C. J., Karanjawala Z. E., Sheppeck J. E., Hager D. C., Aydin N., ibid., 61, 3616-3622 (1996); Leeruff E., Xi F. D., Qie J. H., ibid., 61, 1547-1550 (1996); Altmann H., Kesselring R., Pieles U., Tetrahedron., 52, 12699-12722 (1996); Obara T., Shuto S., Saito Y., Snkeck R., Andrei G., Balzarini J., Deckercq E., Matsuda A., J. Med. Chem., 39, 3847-3852 (1996); Theil F., Ballschuh S., Vonjantalipinski M., Johnson R. A., J. Chem. Soc. Perkin Trans. 1, 1996, 255-258; Biadatti T., Esker J. L., Johnson C. R., Tetrahedron Asymmetry, 7, 2313-2320 (1996), and other references cited therein.
15. Bianco A., Mazzei R. A., Tetrahedron Lett., 38, 6433-6436 (1997); Zhang D. Y., Ghosh A., Suling C., Miller M. J., ibid., 37, 3799-3802 (1996); Jeong L. S., Marquez V. E., ibid., 37, 2353-2356 (1996); Tanaka M., Norimine Y., Fujita T., Suemune H., Sakai K., J. Org. Chem., 61, 6952-6957 (1996); Boyer S. J., Leahy J. W., ibid., 62, 3976-3980 (1997); Martins L. E., Nugent W. A., Jacobsen E. N., ibid., 61, 7963-7966 (1996); Deardorff D. R., Savin K. A., Justman C. J., Karanjawala Z. E., Sheppeck J. E., Hager D. C., Aydin N., ibid., 61, 3616-3622 (1996); Leeruff E., Xi F. D., Qie J. H., ibid., 61, 1547-1550 (1996); Altmann H., Kesselring R., Pieles U., Tetrahedron., 52, 12699-12722 (1996); Obara T., Shuto S., Saito Y., Snkeck R., Andrei G., Balzarini J., Deckercq E., Matsuda A., J. Med. Chem., 39, 3847-3852 (1996); Theil F., Ballschuh S., Vonjantalipinski M., Johnson R. A., J. Chem. Soc. Perkin Trans. 1, 1996, 255-258; Biadatti T., Esker J. L., Johnson C. R., Tetrahedron Asymmetry, 7, 2313-2320 (1996), and other references cited therein.
16. Bianco A., Mazzei R. A., Tetrahedron Lett., 38, 6433-6436 (1997); Zhang D. Y., Ghosh A., Suling C., Miller M. J., ibid., 37, 3799-3802 (1996); Jeong L. S., Marquez V. E., ibid., 37, 2353-2356 (1996); Tanaka M., Norimine Y., Fujita T., Suemune H., Sakai K., J. Org. Chem., 61, 6952-6957 (1996); Boyer S. J., Leahy J. W., ibid., 62, 3976-3980 (1997); Martins L. E., Nugent W. A., Jacobsen E. N., ibid., 61, 7963-7966 (1996); Deardorff D. R., Savin K. A., Justman C. J., Karanjawala Z. E., Sheppeck J. E., Hager D. C., Aydin N., ibid., 61, 3616-3622 (1996); Leeruff E., Xi F. D., Qie J. H., ibid., 61, 1547-1550 (1996); Altmann H., Kesselring R., Pieles U., Tetrahedron., 52, 12699-12722 (1996); Obara T., Shuto S., Saito Y., Snkeck R., Andrei G., Balzarini J., Deckercq E., Matsuda A., J. Med. Chem., 39, 3847-3852 (1996); Theil F., Ballschuh S., Vonjantalipinski M., Johnson R. A., J. Chem. Soc. Perkin Trans. 1, 1996, 255-258; Biadatti T., Esker J. L., Johnson C. R., Tetrahedron Asymmetry, 7, 2313-2320 (1996), and other references cited therein.
17. Bianco A., Mazzei R. A., Tetrahedron Lett., 38, 6433-6436 (1997); Zhang D. Y., Ghosh A., Suling C., Miller M. J., ibid., 37, 3799-3802 (1996); Jeong L. S., Marquez V. E., ibid., 37, 2353-2356 (1996); Tanaka M., Norimine Y., Fujita T., Suemune H., Sakai K., J. Org. Chem., 61, 6952-6957 (1996); Boyer S. J., Leahy J. W., ibid., 62, 3976-3980 (1997); Martins L. E., Nugent W. A., Jacobsen E. N., ibid., 61, 7963-7966 (1996); Deardorff D. R., Savin K. A., Justman C. J., Karanjawala Z. E., Sheppeck J. E., Hager D. C., Aydin N., ibid., 61, 3616-3622 (1996); Leeruff E., Xi F. D., Qie J. H., ibid., 61, 1547-1550 (1996); Altmann H., Kesselring R., Pieles U., Tetrahedron., 52, 12699-12722 (1996); Obara T., Shuto S., Saito Y., Snkeck R., Andrei G., Balzarini J., Deckercq E., Matsuda A., J. Med. Chem., 39, 3847-3852 (1996); Theil F., Ballschuh S., Vonjantalipinski M., Johnson R. A., J. Chem. Soc. Perkin Trans. 1, 1996, 255-258; Biadatti T., Esker J. L., Johnson C. R., Tetrahedron Asymmetry, 7, 2313-2320 (1996), and other references cited therein.
18. Bianco A., Mazzei R. A., Tetrahedron Lett., 38, 6433-6436 (1997); Zhang D. Y., Ghosh A., Suling C., Miller M. J., ibid., 37, 3799-3802 (1996); Jeong L. S., Marquez V. E., ibid., 37, 2353-2356 (1996); Tanaka M., Norimine Y., Fujita T., Suemune H., Sakai K., J. Org. Chem., 61, 6952-6957 (1996); Boyer S. J., Leahy J. W., ibid., 62, 3976-3980 (1997); Martins L. E., Nugent W. A., Jacobsen E. N., ibid., 61, 7963-7966 (1996); Deardorff D. R., Savin K. A., Justman C. J., Karanjawala Z. E., Sheppeck J. E., Hager D. C., Aydin N., ibid., 61, 3616-3622 (1996); Leeruff E., Xi F. D., Qie J. H., ibid., 61, 1547-1550 (1996); Altmann H., Kesselring R., Pieles U., Tetrahedron., 52, 12699-12722 (1996); Obara T., Shuto S., Saito Y., Snkeck R., Andrei G., Balzarini J., Deckercq E., Matsuda A., J. Med. Chem., 39, 3847-3852 (1996); Theil F., Ballschuh S., Vonjantalipinski M., Johnson R. A., J. Chem. Soc. Perkin Trans. 1, 1996, 255-258; Biadatti T., Esker J. L., Johnson C. R., Tetrahedron Asymmetry, 7, 2313-2320 (1996), and other references cited therein.
19. Tanaka M., Yoshioka M., Sakai K., J. Chem. Soc. Chem. Commun., 1992, 1454-1455; idem, Tetrahedron Asymmetry, 4, 981-996 (1993).
20. Tanaka M., Yoshioka M., Sakai K., J. Chem. Soc. Chem. Commun., 1992, 1454-1455; idem, Tetrahedron Asymmetry, 4, 981-996 (1993).
21. PFL has been reclassified as P. cepacia lipase (PCL, Amano PS). However, we use the former name for the sake of uniformity with previous results.
22. 1H-NOESY and COSY NMR spectra. NOE correlations between C4-H (δ4.69), C2-H (δ3.42) and C6β-H (δ3.01) were observed, which suggested that the orientation of methyl group at C-4 position is equatorial in the chair form of the six-membered ring (C2-C7).