Synthesis of a lactone diastereomer of the cembranolide uprolide D

Organic Letters

Volumn 12, Issue 19, 2010, Pages 4328-4331

  Marshall, James A ^a   Griot, Céline A ^a   Chobanian, Harry R ^a,c   Myers, William H ^b  

^a UNIVERSITY OF VIRGINIA   (United States)

^b UNIVERSITY OF RICHMOND   (United States)

^c MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BRIDGED COMPOUND; CHELATING AGENT; LACTONE; ORGANIC COMPOUND; UPROLIDE D;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

BRIDGED COMPOUNDS; CHELATING AGENTS; LACTONES; MOLECULAR STRUCTURE; ORGANIC CHEMICALS; STEREOISOMERISM;

EID: 77957165640     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101776e     Document Type: Article

References (19)

1. Rodríguez, A. D.; Soto, J. J.; Pina, I. C. J. Nat. Prod. 1995, 58, 1209
2. Marshall, J. A.; Chobanian, H. R. Org. Lett. 2003, 5, 1931
3. Semmelhack, M. F.; Wu, E. S. C. J. Am. Chem. Soc. 1976, 98, 3384
4. Semmelhack, M. F.; Tomesch, J. C.; Czarny, M.; Boettger, S. J. Org. Chem. 1978, 43, 1259
5. Bryan, V. J.; Chan, T. H. Tetrahedron Lett. 1996, 37, 5341
6. Tu, Y.; Frohn, M.; Wang, Z.-X.; Shi, Y. Org. Synth. 2003, 80, 1
7. Wang, Z.-X.; Shu, L.; Frohn, M.; Tu, Y.; Shi, Y. Org. Synth. 2003, 80, 9
8. Drewes, S. E.; Hoole, R. F. A. Synth. Commun. 1985, 15, 1067
9. Hoffmann, H. R. M.; Rabe, J. J. Org. Chem. 1985, 50, 3849
10. Still, C. W.; Mobilio, D. J. Org. Chem. 1983, 48, 4785
11. Rayner, C. M.; Astles, P. C.; Paquette, L. A. J. Am. Chem. Soc. 1992, 114, 3926
12. Review: Denmark, S. E.; Almstead, N. G. Allylation of Carbonyls: Methodology and Stereochemistry. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; pp 369 - 370, 376, 386-388.
13. For the structure determination of these lactones, see Supporting Information.
14. Lactone 20 was submitted to NCI for biological evaluation, but after preliminary screening, it was not selected for futher testing.
15. Paquette and co-workers have studied indium-initiated Barbier reactions of methyl (Z)-2-bromomethylpropenoate to various α-silyloxy and benzyloxy aldehydes in aqueous media. These additions also proceed by anti-Felkin-Anh transition states.
16. Isaac, M. B.; Paquette, L. A. J. Org. Chem. 1997, 62, 5333
17. Roush, W. R. J. Org. Chem. 1991, 56, 4151
18. Review: Roush, W. R. Allylorganometallics. In Comprehensive Organic Synthesis; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 1, pp 24 - 27.
19. A likely precursor to an uprolide analogue of structure 20, bis-12,13- epi -eupalmerin acetate, was isolated in 1993 by Rodríguez and Dhasmana: Rodríguez, A. D.; Dhasmana, H. J. Nat. Prod. 1993, 56, 564