Efficient synthesis of an enantiomeric pair of pinidine: An illustration of organochemical carving on the rigid bridged system as the stereochemical tactics

Tetrahedron Letters

Volumn 37, Issue 28, 1996, Pages 4987-4990

  Momose, Takefumi ^a   Nishio, Takashi ^a   Kirihara, Masayuki ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID;

ARTICLE; COLUMN CHROMATOGRAPHY; DRUG ACTIVITY; DRUG SYNTHESIS; ENANTIOMER; PROTON TRANSPORT; STEREOCHEMISTRY;

EID: 0030575390     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00990-2     Document Type: Article

References (20)

1. 1. T. Momose, N. Toyooka, Y. Hirai, Chem. Lett. 1990, 1319-1322; T. Momose, N. Toyooka, S. Seki, Y. Hirai, Chem. Pharm. Bull. 1990, 38, 2072-2074; T. Momose, K. Okumura, H. Tsujimori, K. Inokawa, G. Tanabe, O. Muraoka, Heterocycles 1993, 36, 7-11; O. Muraoka, K. Okumura, T. Maeda, G. Tanabe, T. Momose, Tetrahedron: Asymmetry 1994, 5, 317-320.
2. 1. T. Momose, N. Toyooka, Y. Hirai, Chem. Lett. 1990, 1319-1322; T. Momose, N. Toyooka, S. Seki, Y. Hirai, Chem. Pharm. Bull. 1990, 38, 2072-2074; T. Momose, K. Okumura, H. Tsujimori, K. Inokawa, G. Tanabe, O. Muraoka, Heterocycles 1993, 36, 7-11; O. Muraoka, K. Okumura, T. Maeda, G. Tanabe, T. Momose, Tetrahedron: Asymmetry 1994, 5, 317-320.
3. 1. T. Momose, N. Toyooka, Y. Hirai, Chem. Lett. 1990, 1319-1322; T. Momose, N. Toyooka, S. Seki, Y. Hirai, Chem. Pharm. Bull. 1990, 38, 2072-2074; T. Momose, K. Okumura, H. Tsujimori, K. Inokawa, G. Tanabe, O. Muraoka, Heterocycles 1993, 36, 7-11; O. Muraoka, K. Okumura, T. Maeda, G. Tanabe, T. Momose, Tetrahedron: Asymmetry 1994, 5, 317-320.
4. 1. T. Momose, N. Toyooka, Y. Hirai, Chem. Lett. 1990, 1319-1322; T. Momose, N. Toyooka, S. Seki, Y. Hirai, Chem. Pharm. Bull. 1990, 38, 2072-2074; T. Momose, K. Okumura, H. Tsujimori, K. Inokawa, G. Tanabe, O. Muraoka, Heterocycles 1993, 36, 7-11; O. Muraoka, K. Okumura, T. Maeda, G. Tanabe, T. Momose, Tetrahedron: Asymmetry 1994, 5, 317-320.
5. 2. T. Masamune, H. Matsue, H. Murase, Bull. Chem. Soc. Jpn. 1979, 52, 127-134; R. S. Garigipati, D. M. Tschaen, S. M. Weinreb, J. Am. Chem. Soc. 1990, 112, 3475-3482; H. Nagaoka, K. Shibuya, Y. Yamada, Tetrahedron Lett. 1993, 34, 1501-1504.
6. 2. T. Masamune, H. Matsue, H. Murase, Bull. Chem. Soc. Jpn. 1979, 52, 127-134; R. S. Garigipati, D. M. Tschaen, S. M. Weinreb, J. Am. Chem. Soc. 1990, 112, 3475-3482; H. Nagaoka, K. Shibuya, Y. Yamada, Tetrahedron Lett. 1993, 34, 1501-1504.
7. 2. T. Masamune, H. Matsue, H. Murase, Bull. Chem. Soc. Jpn. 1979, 52, 127-134; R. S. Garigipati, D. M. Tschaen, S. M. Weinreb, J. Am. Chem. Soc. 1990, 112, 3475-3482; H. Nagaoka, K. Shibuya, Y. Yamada, Tetrahedron Lett. 1993, 34, 1501-1504.
8. 3. M. Kirihara, S. Yokoyama, H. Kakuda, T. Momose, Tetrahedron Lett. 1995, 36, 6907-6910.
9. 4. W. H. Tallent, V. L. Stromberg, E. C. Horning, J. Am. Chem. Soc. 1955, 77, 6361-6364; W. H. Tallent, E. C. Horning, ibid. 1956, 78, 4467-4469; R. K. Hill, T. H. Chan, J. A. Joule, Tetrahedron 1965, 21 147-161.
10. 4. W. H. Tallent, V. L. Stromberg, E. C. Horning, J. Am. Chem. Soc. 1955, 77, 6361-6364; W. H. Tallent, E. C. Horning, ibid. 1956, 78, 4467-4469; R. K. Hill, T. H. Chan, J. A. Joule, Tetrahedron 1965, 21 147-161.
11. 4. W. H. Tallent, V. L. Stromberg, E. C. Horning, J. Am. Chem. Soc. 1955, 77, 6361-6364; W. H. Tallent, E. C. Horning, ibid. 1956, 78, 4467-4469; R. K. Hill, T. H. Chan, J. A. Joule, Tetrahedron 1965, 21 147-161.
12. 5. The first asymmetric synthesis of (-)-pinidine and (+)-pinidine: N. Yamazaki, C. Kibayashi, J. Am. Chem. Soc. 1989, 111, 1396-1408.
13. 6. K. Stach, O. Dold, Arzneim. Forsch. 1962, 12, 1022-1026.
14. 7. Enol silyl ethers (4) were prepared in almost quantitative yields from N-protected norgranatanones by reaction with trimethylsilyl triflate in the presence of triethylamine.
15. 8. R. Shirai, M. Tanaka, K. Koga, J. Am. Chem. Soc. 1986, 108, 543-545; R. Shirai, K. Aoki, D. Sato, H.-D. Kim, M. Murakata, T. Yasukata, K. Koga, Chem. Pharm. Bull. 1994, 42, 690-693.
16. 8. R. Shirai, M. Tanaka, K. Koga, J. Am. Chem. Soc. 1986, 108, 543-545; R. Shirai, K. Aoki, D. Sato, H.-D. Kim, M. Murakata, T. Yasukata, K. Koga, Chem. Pharm. Bull. 1994, 42, 690-693.
17. 9. The PIDA oxidation in methanol was found to give the corresponding methyl ester: M. Kirihara, S. Yokoyama, T. Momose, unpublished results.
18. 3).
19. D= -9.5° (c 5.3 EtOH).
20. D= +9.5° (c 0.20 EtOH).