A Facile Synthesis of a Key Intermediate for (+)-Biotin via Strecker Reaction

Synthesis

Volumn , Issue 15, 2003, Pages 2311-2316

  Mori, Yoshikazu ^a   Kimura, Mayumi ^a   Seki, Masahiko ^a  

^a MITSUBISHI TANABE PHARMA CORPORATION   (Japan)

Author keywords

Amino acids; Amino aldehydes; Biotin; Ring closure; Stereoselectivity; Strecker reaction; Vitamins

Indexed keywords

ALDEHYDES; HYDROLYSIS; PROTEINS; REDUCTION; STEREOCHEMISTRY;

AMIDATION;

SYNTHESIS (CHEMICAL);

2 PHENYL 3 PHENOXYCARBONYLTHIAZOLIDINE 4 CARBALDEHYDE; ALDEHYDE DERIVATIVE; BIOTIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; HYDROLYSIS; STEREOCHEMISTRY; STRECKER REACTION; SYNTHESIS;

EID: 0242571972     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-42399     Document Type: Article

References (27)

1. (a) Mistry, P. S.; Dakshinamurti, K. Vitam. Horm. 1964, 22, 1.
2. (b) Coggeshall, C. J.; Heggers, P. J.; Robson, C. M.; Baker, H. Ann. N. Y. Acad. Sci. 1985, 447, 389.
3. (c) Maebashi, M.; Makino, Y.; Furukawa, Y.; Ohinata, K.; Kimura, S.; Sato, T. J. Clin. Biochem. Nutr. 1993, 14, 211.
4. For a review, see: De Clercq, P. J. Chem. Rev. 1997, 97, 1755.
5. (a) Goldberg, M. W.; Sternbach, L. H. US Patent 2489232, 1949; Chem. Abstr. 1951, 45, 184b.
6. (b) Goldberg, M. W.; Sternbach, L. H. US Patent 248923, 1949; Chem. Abstr. 1951, 45, 186a.
7. (c) Gerecke, M.; Zimmermann, J.-P.; Ashwanden, W. Helv. Chim. Acta 1970, 53, 991.
8. For example, see: (a) Senuma, M.; Fujii, T.; Seto, M.; Okamura, K.; Date, T.; Kinumaki, A. Chem. Pharm. Bull. 1990, 38, 882. (b) Iriuchijima, S.; Hasegawa, K.; Tsuchihashi, G. Agric. Biol. Chem. 1982, 46, 1907. (c) Matsuki, K.; Inoue, H.; Takeda, M. Tetrahedron Lett. 1993, 34, 1167. (d) Chen, F. E.; Huang, Y.-D.; Fu, H.; Cheng, Y.; Zhang, D.-M.; Li, Y.-Y.; Peng, Z.-Z. Synthesis 2000, 2004. (e) Choi, C.; Tian, S.-K.; Deng, L. Synthesis 2001, 1737. (f) Seki, M.; Shimizu, T.; Inubushi, K. Synthesis 2002, 361.
9. For example, see: (a) Senuma, M.; Fujii, T.; Seto, M.; Okamura, K.; Date, T.; Kinumaki, A. Chem. Pharm. Bull. 1990, 38, 882. (b) Iriuchijima, S.; Hasegawa, K.; Tsuchihashi, G. Agric. Biol. Chem. 1982, 46, 1907. (c) Matsuki, K.; Inoue, H.; Takeda, M. Tetrahedron Lett. 1993, 34, 1167. (d) Chen, F. E.; Huang, Y.-D.; Fu, H.; Cheng, Y.; Zhang, D.-M.; Li, Y.-Y.; Peng, Z.-Z. Synthesis 2000, 2004. (e) Choi, C.; Tian, S.-K.; Deng, L. Synthesis 2001, 1737. (f) Seki, M.; Shimizu, T.; Inubushi, K. Synthesis 2002, 361.
10. For example, see: (a) Senuma, M.; Fujii, T.; Seto, M.; Okamura, K.; Date, T.; Kinumaki, A. Chem. Pharm. Bull. 1990, 38, 882. (b) Iriuchijima, S.; Hasegawa, K.; Tsuchihashi, G. Agric. Biol. Chem. 1982, 46, 1907. (c) Matsuki, K.; Inoue, H.; Takeda, M. Tetrahedron Lett. 1993, 34, 1167. (d) Chen, F. E.; Huang, Y.-D.; Fu, H.; Cheng, Y.; Zhang, D.-M.; Li, Y.-Y.; Peng, Z.-Z. Synthesis 2000, 2004. (e) Choi, C.; Tian, S.-K.; Deng, L. Synthesis 2001, 1737. (f) Seki, M.; Shimizu, T.; Inubushi, K. Synthesis 2002, 361.
11. For example, see: (a) Senuma, M.; Fujii, T.; Seto, M.; Okamura, K.; Date, T.; Kinumaki, A. Chem. Pharm. Bull. 1990, 38, 882. (b) Iriuchijima, S.; Hasegawa, K.; Tsuchihashi, G. Agric. Biol. Chem. 1982, 46, 1907. (c) Matsuki, K.; Inoue, H.; Takeda, M. Tetrahedron Lett. 1993, 34, 1167. (d) Chen, F. E.; Huang, Y.-D.; Fu, H.; Cheng, Y.; Zhang, D.-M.; Li, Y.-Y.; Peng, Z.-Z. Synthesis 2000, 2004. (e) Choi, C.; Tian, S.-K.; Deng, L. Synthesis 2001, 1737. (f) Seki, M.; Shimizu, T.; Inubushi, K. Synthesis 2002, 361.
12. For example, see: (a) Senuma, M.; Fujii, T.; Seto, M.; Okamura, K.; Date, T.; Kinumaki, A. Chem. Pharm. Bull. 1990, 38, 882. (b) Iriuchijima, S.; Hasegawa, K.; Tsuchihashi, G. Agric. Biol. Chem. 1982, 46, 1907. (c) Matsuki, K.; Inoue, H.; Takeda, M. Tetrahedron Lett. 1993, 34, 1167. (d) Chen, F. E.; Huang, Y.-D.; Fu, H.; Cheng, Y.; Zhang, D.-M.; Li, Y.-Y.; Peng, Z.-Z. Synthesis 2000, 2004. (e) Choi, C.; Tian, S.-K.; Deng, L. Synthesis 2001, 1737. (f) Seki, M.; Shimizu, T.; Inubushi, K. Synthesis 2002, 361.
13. For example, see: (a) Senuma, M.; Fujii, T.; Seto, M.; Okamura, K.; Date, T.; Kinumaki, A. Chem. Pharm. Bull. 1990, 38, 882. (b) Iriuchijima, S.; Hasegawa, K.; Tsuchihashi, G. Agric. Biol. Chem. 1982, 46, 1907. (c) Matsuki, K.; Inoue, H.; Takeda, M. Tetrahedron Lett. 1993, 34, 1167. (d) Chen, F. E.; Huang, Y.-D.; Fu, H.; Cheng, Y.; Zhang, D.-M.; Li, Y.-Y.; Peng, Z.-Z. Synthesis 2000, 2004. (e) Choi, C.; Tian, S.-K.; Deng, L. Synthesis 2001, 1737. (f) Seki, M.; Shimizu, T.; Inubushi, K. Synthesis 2002, 361.
14. Poetsch, E.; Casutt, M. Chimia 1987, 41, 148.
15. (a) Seki, M.; Hatsuda, M.; Mori, Y.; Yamada, S. Tetrahedron Lett. 2002, 43, 3269.
16. (b) Seki, M.; Mori, Y.; Hatsuda, M.; Yamada, S. J. Org. Chem. 2002, 67, 5527.
17. (a) Doering, W. V. E.; Parikh, J. R. J. Am. Chem. Soc. 1967, 89, 5505.
18. (b) Hamada, Y.; Shioiri, T. Chem. Pharm. Bull. 1982, 30, 1921.
19. The X-ray data of syn-5a have been deposited at the Cambridge Crystallographic Data Centre.
20. Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem. Int. Ed. Engl. 1996, 35, 2708.
21. Kobayashi, S.; Tsuchiya, Y.; Mukaiyama, T. Chem. Lett. 1991, 537.
22. Katritzky, A. R.; Pilarski, B.; Urogdi, L. Synthesis 1989, 949.
23. (a) Shimizu, T.; Seki, M. Tetrahedron Lett 2000, 41, 5099.
24. (b) Shimizu, T.; Seki, M. Tetrahedron Lett. 2001, 42, 429.
25. (c) Shimizu, T.; Seki, M. Tetrahedron Lett. 2002, 43, 1039.
26. (d) Mori, Y.; Seki, M. Heterocycles 2002, 58, 125.
27. Poetsch and Casutt of the Merck Laboratories synthesized the bicyclic intermediate 14 through reduction of a carbonyl group of bicyclic hydantoin 13 derived from L-cysteine followed by formation of the corresponding imidazolide, cyanation and hydrolysis (Scheme 6).5 (Equation presented)