Stereoselective synthesis of the antifungal antibiotic (+)-preussin

Tetrahedron

Volumn 54, Issue 51, 1998, Pages 15673-15678

  Veeresa, G ^a   Datta, Apurba ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Antibiotic; Chelation control; Grignard reaction; Stereoselection

Indexed keywords

ALCOHOL; MAGNESIUM; PHENYLALANINE; PREUSSIN;

ANTIMICROBIAL ACTIVITY; ARTICLE; CHELATION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0032542149     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00981-8     Document Type: Article

References (22)

1. 1. (a) Schwartz, R.E.; Liesch, J.; Hensens, O.; Zitano, L.; Honeycutt, S.; Garrity, G.; Fromtling, R.A.; Onishi, J.; Monaghan, R. J. Antibiot. 1988, 41, 1774-1779.
2. (b) Johnson, J.H.; Phillipson, D.W.; Kahle, A.D.J. Antibiot. 1989, 42, 1184-1185.
3. (c) Schwartz, R.E.; Onishi, J.; Monaghan, R ; Liesch, J.; Hensens, O. US Patent 4, 847, 284, 1989.
4. 2. For the reported syntheses see: (a) Kanazawa, A.; Gillet, S.; Delair, P.; Greene, A.E. J. Org. Chem. 1998, 63 , 4660-4663.
5. (b) Armas, P.D.; Tellado-Garcia, F.; Tellado-Marrero, J.J.; Robles, J. Tetrahedron Lett. 1998, 39, 131-134.
6. (c) Kadota, I.; Saya, S.; Yamamoto, Y. Heterocycles, 1997, 46, 335-348.
7. (d) Schaumann, E.; Beier, C. Synthesis, 1997, 1296-1300.
8. (e) Verma, R.; Ghosh, S.K. J. Chem. Soc.,Chem.Commun. 1997, 1601-1602.
9. (f) Yoda, H.; Yamazaki, H.; Takabe, K. Tetrahedron Asymm. 1996, 7, 373-374.
10. (g) Overhand, M.; Hecht, S.M. J. Org. Chem.1994,59, 4721-4722.
11. (h) Deng, W.; Overman, L.E. J. Am. Chem. Soc. 1994,116, 11241-11250.
12. (i) McGrane, P.L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485-11489.
13. (j) Shimazaki, M.; Okazaki, F.; Nakajima, F.; Ishikawa, T.; Ohta, A. Heterocycles, 1993, 36, 1823-1836.
14. (k) Pak, C.S.; Lee, G.H. J. Org. Chem. 1991, 56, 1128.
15. 3. (a) Denis, J-N.; Correa, A.; Greene, A.E. J. Org. Chem. 1991, 56, 6939-6942.
16. (b) Jayasinghe, L.R.; Datta, A.; Ali, S.M.; Zygmunt, J.; Vander Velde, D.G.; Georg, G.I. J. Med. Chem. 1994, 37, 2981-2984.
17. (c) Ali, S.M.; Hoemann, M.Z.; Aube, J.; Mitscher, L.A.; Georg, G.I.; McCall, R.; Jayasinghe, L.R. J. Med. Chem. 1995, 38, 3821-3828.
18. 4. (a) Veeresa, G.; Datta, A. Tetrahedron Lett. 1997, 38, 5223-5224.
19. (b) Veeresa, G.; Datta, A. Tetrahedron Lett. 1998, 39, 119-122.
20. (c) Veeresa, G.; Datta, A. Tetrahedron Lett. 1998, 39, 3069-3070.
21. 5. Assignment of syn stereochemistry to the major isomer 2, initially based on analogy (ref. 3,4), was proved conclusively by comparing the spectral and analytical data of the subsequent reaction products 11 and 1 with their literature reported values (vide infra).
22. 6. Zhang, Y. L.; Shing, T. K. M. J. Org. Chem. 1997, 62, 2622-2624.