The macrocyclic domain of phorboxazole A. A stereoselective synthesis of the C1-C32 macrolactone

Tetrahedron Letters

Volumn 40, Issue 12, 1999, Pages 2291-2294

  Williams, David R ^a   Clark, Michael P ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; LACTONE DERIVATIVE; MACROLIDE; PHORBOXAZOLE A; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CYCLIZATION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE;

EID: 0033583149     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00210-5     Document Type: Article

References (16)

1. 1. (a) Searle, P.A.; Molinski, T.F. J. Am. Chem. Soc. 1995, 117, 8126.
2. (b) Searle, P.A.; Molinski, T.F.; Leahy, J.; Brzezinski, L.J. J. Am. Chem. Soc. 1996, 118, 9422.
3. (c) Molinski, T. Tetrahedron Lett. 1996, 37, 7879.
4. 2. (a) Pettit, G.R.; Tan, R.; Gao, R.T.; Williams, M.D.; Doubek, D.L.; Boyd, M.R.; Schmidt, J.M.; Chapuis, J.-C.; Hamel, E.; Bai, R.; Hooper, J.N.A.; Tackett, L.P. J. Org. Chem. 1993, 58, 2538.
5. (b) Phorboxazole A has antitumor potency similar to that observed for spongistatin-1. See: Pettit, G.R.; Cichacz, Z.A.; Gao, F.; Herald, C.L.; Boyd, M.R.; Schmidt, J.M.; Hooper, J.N.A. J. Org. Chem. 1993, 58, 1302.
6. 3. Forsyth, C.J.; Ahmed, F.; Cink, R.D.; Lee, C.S. J. Am. Chem. Soc. 1998, 120, 5597.
7. 4. Williams, D.R.; Clark, M.P.; Berliner, M.A. Tetrahedron Lett. 1999, 40, 2287.
8. 5. Kishi, Y.; Negri, D.P. Tetrahedron Lett. 1987, 28, 1063.
9. D).
10. 7. Kocienski, P.J.; Blakemore, P.R.; Cole, W.J.; Morley, A. Synlett. 1998, 26.
11. 2 in EtOH.
12. 9. Kende, A.S.; Mendoza, J.S. Tetrahedron Lett. 1990, 31, 7105.
13. 10. Takano, S.; Hatakeyama, S.; Satoh, K.; Sakurai, K. Tetrahedron Lett. 1987, 28, 2713.
14. 11. Dess, D.B.; Martin, J.C. J. Am. Chem. Soc. 1991, 113, 7277.
15. 12. Still, W.C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405.
16. 1H NMR spectrum. The corresponding E-lactone is characterized by individual multiplets centered at δ 6.59 and δ 5.90. We gratefully acknowledge the assistance of Professor Craig Forsyth (Department of Chemistry, University of Minnesota) for supplying proton NMR spectra for our comparisons.