Enantioselective synthesis of the 4-hydroxy buteneolide terminus of mucocin and related annonaceous acetogenins

Tetrahedron Letters

Volumn 39, Issue 52, 1998, Pages 9627-9628

  Evans, P Andrew ^a   Murthy, V Srinivasa ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOGENIN; MUCOCIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032564609     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02206-0     Document Type: Article

References (13)

1. 1. Marshall, J. A.; Hinkle, K. W.; Hagedorn, C. E. Israel J. Chem. 1997, 37, 97 and pertinent references therein.
2. 2. For alternative approaches to the 4-hydroxy buteneolide terminus, see: (a) Koert, U. Tetrahedron Lett. 1994, 35, 2511.
3. (b) Hoye, T. R.; Hanson, P. R.; Hasenwinkel, L. E.; Ramirez, E. A.; Zhuang, Z. Tetrahedron Lett. 1994, 35, 8529.
4. (c) Hoye, T. R.; Tan, L. Tetrahedron Lett. 1995, 36, 1981.
5. (d) Trost, B. M.; Calkins, T. L. Tetrahedron Lett. 1995, 36, 6021.
6. (e) Wang, T. -L.; Hu, E.; Cassady, J. M. Tetrahedron Lett. 1995, 36, 9301.
7. (f) Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 4876 and pertinent references therein.
8. 3. Shi, G.; Alfonso, D.; Fatope, M. O.; Zeng, L.; Gu, Z. -m.; Zhao, G. -x.; He, K.; MacDougal, J. M.; McLaughlin, J. L. J. Am. Chem. Soc. 1995, 117, 10409.
9. 4. For our synthetic approach to mucocin 1, see Evans, P. A.; Murthy, V. S. Tetrahedron Lett. preceding paper.
10. 13C-NMR) and analytical (HRMS) data in accord with the assigned structure.
11. 6. Bachi, M. D.; Bosch, E. J. Org. Chem. 1992, 57, 4696.
12. 7. Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467.
13. 2b (equation presented) (table presented)