An improved synthesis of the (E,Z)-dienoate precursor of (+)-damavaricin D via a vinylogous Horner-Wadsworth-Emmons reaction

Tetrahedron Letters

Volumn 40, Issue 7, 1999, Pages 1269-1272

  Chemler, Sherry R ^a,b   Coffey, D Scott ^a,b   Roush, William R ^a,b  

^a UNIVERSITY OF MICHIGAN   (United States)

^b INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; DAMAVARICIN D; MACBECIN I; PHOSPHONIC ACID DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STEREOCHEMISTRY; SYNTHESIS; THERMODYNAMICS;

EID: 0033547964     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02638-0     Document Type: Article

References (14)

1. Roush, W. R.; Coffey, D. S.; Madar, D. J. J. Am. Chem. Soc. 1997, 119, 11331.
2. Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405.
3. Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masamune, S.; Roush, W. R.; T. Sakai, T. Tetrahedron Lett. 1984, 25, 2183.
4. Palkowitz, A. D. Ph. D. Thesis, MIT, 1990.
5. Evans, D. A.; Miller, S. J.; Ennis, M. D. J. Org. Chem. 1993, 58, 471.
6. Letham, D. S.; Young, H. Phytochemistry 1971, 10, 2077.
7. Hughes, D. L. Org. Reactions 1992, 42, 335.
8. Gao, L.-x.; Murai, A. Tetrahedron Lett. 1992, 33, 4349.
9. Trehan, A.; Mirzadegan, T.; Liu, R. S. H. Tetrahedron 1990, 46, 3769.
10. Dangles, O.; Guibe, F.; Balavoine, G. J. Org. Chem. 1987, 52, 4984.
11. Ninomiya, K.; Shioiri, T.; Yamada, S. Tetrahedron 1974, 30, 2151.
12. Scheidt, K. A.; Chen, H.; Follows, B. C.; Chemler, S. R.; Coffey, D. S.; Roush, W. R. J. Org. Chem. 1998, 63, 6463.
13. Tidwell, T. T. Synthesis 1990, 857.
14. Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863.