A modular approach to marine macrolide construction. 1. An enantiocontrolled route to the C1-C12 (AB) spiroacetal sector

Tetrahedron Letters

Volumn 38, Issue 29, 1997, Pages 5115-5118

  Paquette, Leo A ^a   Zuev, Dmitry ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MACROLIDE;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030741324     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01140-4     Document Type: Article

References (19)

1. (a) Pettit, G. R.; Chichacz, Z. A.; Gao, F.; Herald, C. L; Boyd, M. R.; Schmidt, J. M.; Hooper, J. N. A. J. Org. Chem. 1993, 58, 1302.
2. (b) Pettit, G. R.; Cichacz, Z. A.; Gao, F.; Herald, C. L.; Boyd, M. R. J. Chem. Soc., Chem. Commun. 1993, 1166.
3. (c) Pettit, G. R.; Herald, C. L.; Cichacz, Z. A.; Gao, F.; Schmidt, J. M.; Boyd, M. R.; Christie, N. D.; Boettner, F. E. J. Chem. Soc., Chem. Commun. 1993, 1805.
4. (d) Pettit, G. R.; Cichacz, Z. A.; Herald, C. L.; Gao, F.; Boyd, M. R.; Schmidt, J. M.; Hamel, E.; Bai, R. J. Chem. Soc., Chem. Commun. 1994, 1605.
5. (e) Pettit, G. R. Pure Appl. Chem. 1994, 66, 2271.
6. (a) Kobayashi, M.; Aoki, S.; Kitagawa, I. Tetrahedron Lett. 1994, 35, 1243.
7. (b) Kobayashi, M.; Aoki, S.; Sakai, H.; Kawazoe, K.; Kihara, N.; Sasaki, T.; Kitagawa, I. Tetrahedron Lett. 1993, 34, 2795.
8. (c) Kobayashi, M.; Aoki, S.; Sakai, H.; Kihara, N.; Sasaki, T.; Kitagawa, I. Chem. Pharm. Bull. 1993, 41, 989.
9. (d) Kobayashi, M.; Aoki, S.; Gato, K.; Kitagawa, I. Chem. Pharm. Bull. 1996, 44, 2142.
10. Fusetani, N.; Shinoda, K.; Matsunaga, S. J. Am. Chem. Soc. 1993, 115, 3977.
11. Claffey, M. M.; Heathcock, C. H. J. Org. Chem. 1996, 61, 7646.
12. Paterson, I.; Oballa, R. M.; Norcross, R. D. Tetrahedron Lett. 1996, 37, 8581.
13. Nagao, Y.; Hagiwara, Y.; Kumagai, T.; Ochiai, M.; Inoue, T.; Hashimoto, K.; Fujita, E. J. Org. Chem. 1986, 51, 2391.
14. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815.
15. Paterson, I.; Gibson, K. R.; Oballa, R. M. Tetrahedron Lett. 1996, 37, 8585.
16. 2O, 90 °C.
17. Nambiar, K. P.; Mitra, A. Tetrahedron Lett. 1994, 35, 3033.
18. 6) ppm 170.1, 160.1, 139.1, 132.8, 131.1, 129.7, 129.4, 129.1, 128.0, 122.7, 114.5, 98.6, 73.4, 72.8, 72.7, 67.9, 66.9, 65.5, 64.7, 61.6, 55.1, 40.7, 39.0, 37.8, 36.7, 31.1, 21.6.
19. 6) ppm 160.0, 139.0, 132.9, 131.6, 129.8, 129.6, 129.1, 127.8, 123.0, 114.4, 99.3, 74.0, 73.6, 72.7, 68.3, 68.1, 66.4, 65.1, 63.0, 55.1, 47.4, 42.1, 41.5, 39.5, 36.5, 31.1, 26.5, 18.7, -4.2, -4.5.