First asymmetric total synthesis of synerazol, an antifungal antibiotic, and determination of its absolute stereochemistry

Journal of Organic Chemistry

Volumn 70, Issue 14, 2005, Pages 5643-5654

  Hayashi, Yujiro ^a   Shoji, Mitsuru ^a   Mukaiyama, Takasuke ^a   Gotoh, Hiroaki ^a   Yamaguchi, Shinpei ^a   Nakata, Munetaka ^b   Kakeya, Hideaki ^c   Osada, Hiroyuki ^c  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

^b TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

^c Japan Science and Technology Agency   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTICS; BENZENE; ETHERS; STEREOCHEMISTRY; SUBSTRATES;

ANTIFUNGAL; DIASTEREOMERS; RACEMIZATION-FREE DEPROTECTION; SYNERAZOL;

SYNTHESIS (CHEMICAL);

ANTIFUNGAL AGENT; BENZYLIDENE DERIVATIVE; DESS MARTIN PERIODINANE; DIMETHYL ETHER; FUNCTIONAL GROUP; POTASSIUM PERCHLORATE; SILANE DERIVATIVE; SYNERAZOLE; TRIISOPROPYLSILYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; DEPROTECTION REACTION; DIASTEREOISOMER; OXIDATION; RACEMIZATION; STEREOCHEMISTRY;

ANTIBIOTICS, ANTIFUNGAL; BENZYLIDENE COMPOUNDS; MOLECULAR CONFORMATION; OXIDATION-REDUCTION; PYRROLIDINONES; STEREOISOMERISM;

EID: 22144441375     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050664x     Document Type: Article

References (26)

1. Ando, O.; Satake, H.; Nakajina, M.; Sato, A.; Nakamura, T.; Kinoshita, T.; Furuya, K.; Haneishi, T. J. Antibiot. 1991, 44, 382.
2. (a) Bloch, P.; Tamm, C.; Bollinger, P.; Petcher, T. J.; Weber, H. P. Helv. Chim. Acta 1976, 59, 133.
3. (b) Weber, H. P.; Petcher, T. J.; Bloch, P.; Tamm, C. Helv. Chim. Acta 1976, 59, 137.
4. (c) Wenke, J.; Anke, H.; Sterner, O. Biosci. Biotechnol. Biochem. 1993, 57, 961.
5. (d) Komagata, D.; Fujita, S.; Yamashita, N.; Saito, S.; Morino, T. J. Antibiot. 1996, 49, 958.
6. Asami, Y.; Kakeya, H.; Onose, R.; Yoshida, A.; Matsuzaki, H.; Osada, H. Org. Lett. 2002, 4, 2845.
7. For synthetic studies on the pseurotins, see: (a) Dolder, M.; Shao, X.; Tamm, C. Helv. Chim. Acta 1990, 73, 63.
8. (b) Shao, X.; Dolder, M.; Tamm, C. Helv. Chim. Acta 1990, 73, 483.
9. (c) Su, Z.; Tamm, C. Helv. Chim. Acta 1995, 78, 1278.
10. (d) Su, Z.; Tamm, C. Tetrahedron 1995, 51, 11177.
11. (e) Aoki, S.; Ohi, T.; Shimizu, K.; Shiraki, R.; Takao, K.; Tadano, K. Heterocycles 2002, 58, 57.
12. Hayashi, Y.; Shoji, M.; Yamaguchi, J.; Sato, K.; Yamaguchi, S.; Mukaiyama, T.; Sakai, K.; Asami, Y.; Kakeya, H.; Osada, H. J. Am. Chem. Soc. 2002, 124, 12078.
13. Hayashi, Y.; Shoji, M.; Yamaguchi, S.; Mukaiyama, T.; Yamaguchi, J.; Kakeya, H.; Osada, H. Org. Lett. 2003, 5, 2287.
14. (a) Aoki, S.; Ohi, T.; Shimizu, K.; Shiraki, R.; Takao, K.; Tadano, K. Heterocycles 2004, 62, 161.
15. (b) Aoki, S.; Ohi, T.; Shimizu, K.; Shiraki, R.; Takao, K.; Tadano, K. Bull. Chem. Soc. Jpn. 2004, 77, 1703.
16. We have orally presented the first synthesis of synerazol and determination of its absolute stereochemistry at the following meeting: Hayashi, Y.; Shoji, M.; Mukaiyama, T.; Yamaguchi, S.; Gotoh, H.; Kakeya, H.; Osada, H. Abstracts of Papers, 84 Annual Meeting of Japan Chemical Society, Kobe, Japan, March 27, 2004; p 981.
17. Igarashi, Y.; Yabuta, Y.; Furumai, T. J. Antibiot. 2004, 57, 537.
18. Saito, S.; Komada, K.; Morowake, T. Org. Synth. 1995, 73, 184.
19. (a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
20. (b) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
21. (c) Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
22. (d) Meyer, S. D.; Schreiber, S. L. J. Org. Chem. 1994, 59, 7549.
23. (a) Adam, W.; Bialas, J.; Hadjiarapoglou, L. Chem. Ber. 1991, 124, 2377.
24. (b) Koseki, Y.; Kusano, S.; Ichi, D.; Yoshida, K.; Nagasaka, T. Tetrahedron 2000, 56, 8855.
25. Greene, A. E.; Drian, C. L.; Crabbe, P. J. Am. Chem. Soc. 1980, 102, 7583.
26. HPLC analysis conditions: CHIRACEL AD-H column, 2-PrOH/ hexane = 1/3, 1.0 mL/min; retention times, 12.82 min (4 + natural synerazol), 13.00 min, 13.65 min (5 + natural synerazol).