Stereoselective synthesis of 19-hydroxytaxoid using intramolecular pinacol coupling reaction

Chemistry Letters

Volumn 33, Issue 11, 2004, Pages 1412-1413

  Mukaiyama, Teruaki ^a,b   Ogawa, Yasuyuki ^a,b   Kuroda, Kiichi ^a,b   Matsuo, Jun Ichi ^a,b  

^a KITASATO INSTITUTE   (Japan)

^b KITASATO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DIKETONE; TAXOID; TITANIUM;

ANALYTIC METHOD; ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; OLEFINATION; PINACOL REARRANGEMENT; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 13544254555     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2004.1412     Document Type: Article

References (19)

1. J. L. McLaughlin, R. W. Miller, R. G. Powell, and C. R. Smith, Jr., J. Nat. Prod., 44, 312 (1981).
2. a) T. Mukaiyama, I. Shiina, H. Iwadare, H. Sakoh, Y. Tani, M. Hasegawa, and K. Saitoh, Proc. Jpn. Acad., 73B, 95 (1997).
3. b) T. Mukaiyama, I. Shiina, H. Iwadare, M. Saitoh, T. Nishimura, N. Ohkawa, H. Sakoh, K. Nishimura, Y. Tani, M. Hasegawa, K. Yamada, and K. Saitoh, Chem. - Eur. J., 5, 121 (1999).
4. a) T. Mukaiyama, H. Arai, and I. Shiina, Chem. Lett., 2000, 580.
5. b) T. Mukaiyama, K. Pudhom, K. Yamane, and H. Arai, Bull. Chem. Soc. Jpn., 76, 413 (2003).
6. a) K. Pudhom, H. Arai, K. Yamane, and T. Mukaiyama, Chem. Lett., 2002, 82.
7. b) K. Pudhom, J. Matsuo, and T. Mukaiyama, Heterocycles, 59, 445 (2003) .
8. c) J. Matsuo, Y. Ogawa, K. Pudhom, and T. Mukaiyama, Chem. Lett., 33, 124 (2004).
9. The numbers on each carbon atom of all intermediates are according to IUPAC taxane skeleton nomenclature.
10. 3 by a literature method: a) R. C. Paul, A. Arneja, and S. P. Narula, Inorg. Nucl. Chem. Lett., 5, 1013 (1969). b) S. P. Narula and H. K. Sharma, Inorg. Synth., 24, 181 (1986). c) T. Mukaiyama, A. Kagayama, and I. Shiina, Chem. Lett., 1998, 1107.
11. 3 by a literature method: a) R. C. Paul, A. Arneja, and S. P. Narula, Inorg. Nucl. Chem. Lett., 5, 1013 (1969). b) S. P. Narula and H. K. Sharma, Inorg. Synth., 24, 181 (1986). c) T. Mukaiyama, A. Kagayama, and I. Shiina, Chem. Lett., 1998, 1107.
12. 3 by a literature method: a) R. C. Paul, A. Arneja, and S. P. Narula, Inorg. Nucl. Chem. Lett., 5, 1013 (1969). b) S. P. Narula and H. K. Sharma, Inorg. Synth., 24, 181 (1986). c) T. Mukaiyama, A. Kagayama, and I. Shiina, Chem. Lett., 1998, 1107.
13. J. Ishihara, R. Nonaka, Y. Terasawa, R. Shiraki, K. Yabu, H. Kataoka, Y. Ochiai, and K. Tadano, J. Org. Chem., 63, 2679 (1998).
14. a) J. M. Denis, C. Girard, and J. M. Conia, Synthesis, 1972, 549.
15. b) T. Tokoroyama, K. Matsuo, and R. Kanazawa, Bull. Chem. Soc. Jpn., 53, 3383 (1980).
16. a) E. Block, Org. React., 30, 457 (1984).
17. b) E. J. Corey, F. A. Carey, and R. A. E. Winter, J. Am. Chem. Soc., 87, 934 (1965).
18. c) E. J. Corey and P. B. Hopkins, Tetrahedron Lett., 23, 1979 (1982).
19. Kuwajima et al. already reported this taxoid as an intermediate for synthesis of taxol; H. Kusama, R. Hara, S. Kawahara, T. Nishimori, H. Kashima, N. Nakamura, K. Morihira, and I. Kuwajima, J. Am. Chem. Soc., 122, 3811 (2000).