Ayhan S. DEMİR, Haluk HAMAMCI, Aksoy Hilal CAM, Nurettin CAMKERTEN, Fatoş DOĞANEL

An efficient synthesis of (1S, 2R)-1-amino-2-indanol, a key intermediate of HIV protease inhibitor, indinavir

(1S,2R)-l-amino-2-indanol, a key component of an HIV protease inhibitor is synthesized in four steps starting from indanone. The Mn(OAC)s mediated acetoxylation of indanone followed by fungus catalyzed hydrolysis of acetoxyindanone furnished optically pure a-hydroxy indanone. Formation and enantioselective reduction of oxime ether of 2-hydroxyindanone afforded (1S, 2R)-l-amino-2-indanol in 97% cis selectivity.

PDF

___

1. (a) I. W. Davies, C. H. Senanayake, R. D. Larsen, T. R. Verhoven, P. J. Reider, Tetrahedron Lett. 1996, 37, 813. (b) Y. Hong, Y. Gao, X. Nie, C. M. Zeep, Tetrahedron lett. 1994, 35, 6631. (c) B. D. Simone, D. Savoia, E. Tagliavini, Umani-Ronchi, Tetrahedron: Asymmetry 1995, 6, 301.
2. (a) A. K. Ghosh, M. Onishi, J. Am. Chem. Soc. 1996, 118, 2527. (b) A. K. Ghosh, M. Onishi, Tetrahedron: Asymmetry 1996, 7, 375. (c) I. W. Dawies, C. H. Senanayake, L. Castonguay, R. D. Larsen, T. R. Verhoven, P. J. Reider, Tetrahedron Lett.1995, 36, 7619. (d) A. K. Ghosh, W. Liu, J. Org. Chem. 1996, 61, 6175. (e) A. K. Ghosh, Y. Chen, Tetrahedron Lett. 1995, 38, 6811. (f) N. Zeng, Armstrob III, J. C. McWilliams, R. P. Volante, Tetrahedron Lett. 1997, 38, 2817.
3. (a) J. P. Vacca, B. D. Dorsey, W. A. Schleif, R. B. Levin, S. L. McDaniel, P. L. Darke, J. Zugay, J. C. Quintero, O. M. Blahy, E. Roth, V. V. Sardana, A. J. Schlabach, P. I. Graham, J. H. Condra, L. Gotlieb, M. K. Holloway, J. Lin, I. -W. Chen, K. Vastag, D. Ostovic, P. S. Anderson, E. A. Emini, J. R. Huff, Proc. Natl. Acad. Sci. USA, 1994, 91, 4096. (b) Idem, J. Med Chem. 1994, 37 3443, and references.
4. Synthesis of cis-amino alcohol: (a) H. Kajiro, S. Mitamura, A. Mori, T. Hiyama, Synlett 1998, 51. (b) E. didier, B. Loibinoux, G. M. R. Tombo, G. Rihs, Tetrahedron1991, 47, 4941. (c) D. Askin, K. K. Eng, K. Rossen, R. M. Purick, K. K. Wells, R. P. Volante, P. J. Rieder, Tetrahedron Lett. 1994, 35, 673. (d) C. H. Senanayake, L. J. DiMichele, L. E. Fredenburgh, K. M. Ryan, F. E. Roberts, R. D. Larsen, T. R. Verhoeven, P. J. Reider, Tetrahedron Lett. 1995, 36, 7615. (e) M. K. Lakshman, B. Zawc, Tetrahedron Lett. 1996, 37, 2529. (f) C. H. Senanayake, Aldrichimica Acta, 1998, 31, 3.
5. A. S. Demir, A. Saatçioğlu, Synthetic Commun. 1993, 23(5), 571. (b) A. S. Demir, A. Jeganathan, Synthesis, 1992, 235. (c) A. S. Demir, N. Çamkerten, H. akgün, C. Tanyeli, A. S. Mahasneh, D. S. Watt, Synthetic Commun. 1990, 20(15), 2279. (d) A. S. Demir, T. Sayraç, D. S. Watt, Synthesis 1990, 1119. (e) a. S. Demir, H. Akgün, CÇ. Tanyeli, D. S. Watt, Synthesis 1991, 719. (f) a. S. Demir, C. Tanyeli, H. akgün, Z. Çalişkan, E. Özgül, Bull. Chem. Soc. Fr. 1995, 132, 423. (g) A. S. Demir C. Tanyeli, V. Gülbeyaz, H. Akgün Turkish J. Chemistry 1996, 20, 244. (h) C. Tanyeli, Z. Çalişkan, A. S. Demir Synthetic Commun. 1997, 27(19), 3471. (i) A. Chretien, G. Varga, Bull. Soc. Chim. Fr. 1936, 3, 2385. (j) G. Bauer, “Handbuch der Praeparativen anorganischen Chemie”, Stuttgart, 1962, p. 1283. (k) G. I. Nikishin, M. G. Vinogradov, S. P. Verenchikov, Izv. Akad. Nauk SSSR Ser. Khim.1969, 1835, Bull Acad. Sci. USSR Div. Chem. Sci. 1969, 1698.
6. A. S. Demir, H. Hamamci, C. Tanyeli, I. M. Akhmedov, F. Doganel, Tetrahedron: Asymmetry, 1998, 9, 1673.
7. A. S. Demir, C. Tanyeli, A. Cagir, M. N. Tahir, D. Ulku, Tetrahedron:Asymmetry 1998, 9, 1035.
8. Related work for the synthesis of α-hydroxyketones: (a) D. Enders, V. Bushan, Tetrahedon Lett. 1988, 29, 2437. (b) F. A. davis, M. S. Hakue, J. Org. Chem. 1986, 51, 4083. (c) F. A. Davis, A. C. Sheppard, B. Chen, M. S. Hakue, J. Am. Chem. Soc. 1990, 112, 6679, (d) F. A. Davis, C. Clark, A. Kumar, B. Chen, J. Org. Chem. 1994, 59, 1184. (e) W. adam, F. Prechtl, Chem. Ber. 1994, 127, 667. (f) W. Adam, R. T. Fell, V. R. Stegman, C. R. Sha-Moller, J. Am. Chem. Soc. 1998, 120 708. (g) W. Adam, M. T. Diaz, R. T. Fell, C. R. Saha-Moller, Tetrahedron: Asymmetry 1996, 8, 2207. (h) D. Gala, D. J. DiBenedetto, J. E. Clark, B. L. Murphy, D. P. Schumacher, M. Steinman, Tetrahedron Lett. 1996, 37, 611. (i) H. Ota, G. Dobashi, (Yuki Gosei Kogyo Co., Ltd) Jpn. Kokai Tokkyo Koho JP 62, 208, 298 [87, 208, 298] (C1. C12p41/00), 12 Sep 1987, Appl. 86/49, 983, 07 Mar 1986. Ca 108: 148914v. (j) W. Adam, R. T. Fell, C. R. Saha-Moller, C. G. Zhao, Tetrahedron; Asymmetry 1998, 9, 297. (k) H. Kajiro, S. Mitamura, A. Mori, T. Hiyama, Tetrahedron; Asymmetry 1996, 7, 2399.
9. (a) A. Monsadi, M. Gessner, G. Gunther, J. Deger, G. Singer, J. High Res. Chromatography & Chlromatography Commun. 1987, 10 67. (b) K. N. Slessor, G. G. S. King, D. R. Miller, M. L. Winson, T. L. Cutforth, J. Chem. Ecol. 1985, 11, 1659.
10. C-S. Chen, Y. Fujimoto, G. Girdaukas, C. H. Sih, J. Am. Chem. Soc. 1982, 104, 7294.
11. (a) A. S. Demir Pure & Appl. Chem. 1997, 69, 108. (b) F. Doganel, Thesis Middle east Technical University. (c) G. Ocskay, L. Wargha, Tetrahedron 1958, 2, 140. (d) W. Gruber, H. Leditschke, K. Lange, Chem. Ber. 1938, 5, 62. (e) W. Gruber, Can. J. Chem. 1953, 31, 19. (f) H. Gilman, N. O. Calloway, J. Am. Chem. Soc. 1933, 55, 4197. (g) A. S. Demir, C. Tanyeli, E. Altinel, Tetrahedron Lett. 1997, 38, 7267. (h) S. Itsuno, Y. Sakurai, K. Ito, A. Hirao, S. Nakahama, Bull. Chem. Soc. Jpn. 1987, 60, 395. (i) S. Itsuno, A. Hirao, S. Nakahama, Y. Yamazaki, J. Chem. Soc. Perkin I 1983. (j)S. Itsuno, M. Nakano, K. Miyazaki, H. Masuda, K. Ito, J. Chem. Soc. Perkin I 1985, 2039. (k) S. Itsuno, K. Ito, A. Hirao, S. Nakahama, J. Chem. Soc. Chem. Commun. 1983, 469. (l) S. Itsuno, K. Ito, A. Hirao, S. Nakahama, J. Chem. Soc. Perkin I 1984, 2887.
12. A. S. Demir, I. Mecitoğlu, C. Tanyeli, V. Gülbeyaz, Tetrahedron: Asymmetry 1996, 7, 3359.