A concise and modular synthesis of pyranicin

Organic Letters

Volumn 10, Issue 21, 2008, Pages 4955-4957

  Griggs, Nolan D ^a   Phillips, Andrew J ^a  

^a UNIVERSITY OF COLORADO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BUTENOLIDE; DRUG DERIVATIVE; FURAN DERIVATIVE; GAMMA BUTYROLACTONE; LACTONE; PYRANICIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

4-BUTYROLACTONE; FURANS; LACTONES; MOLECULAR STRUCTURE;

EID: 58149154433     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802041c     Document Type: Article

References (29)

1. For a review see: Bermejo, A; Figadere, B.; Zafra-Polo, M.-C.; Barrachina, I; Estornell, E.; Cortes, D. Nat. Prod. Rep. 2005, 22, 269, and references cited therein.
2. Alali, F. Q.; Rogers, L.; Zhang, Y.; McLaughlin, J. L. Tetrahedron 1998, 54, 5833.
3. Keaton, K. A.; Phillips, A. J. J. Am. Chem. Soc. 2006, 128, 408.
4. For other total syntheses see: (a) Strand, D.; Norrby, P.-O.; Rein, T. J. Org. Chem. 2006, 71, 1879.
5. (b) Strand, D.; Rein, T. Org. Lett. 2005, 7, 199.
6. (c) Takahashi, S.; Kubota, A.; Nakata, T. Org. Lett. 2003, 5, 1353.
7. (d) Hattori, Y.; Furuhata, S.-i.; Okajima, M.; Konno, H.; Abe, M.; Miyoshi, H.; Goto, T.; Makabe, H. Org. Lett. 2008, 10, 717.
8. (e) Furuhata, S.-i.; Hattori, Y.; Okajima, M.; Konno, H.; Abe, M.; Miyoshi, H.; Goto, T.; Makabe, H. Tetrahedron 2008, 64, 7695.
9. (a) Henderson, J. A.; Jackson, K. L.; Phillips, A. J. Org. Lett. 2007, 9, 5299.
10. (b) Um, J. M.; Houk, K. N.; Phillips, A. J. Org. Lett. 2008, 10, 3769.
11. (c) See also: Nicolaou, K. C.; Frederick, M. O.; Burtoloso, A. C. B.; Denton, R. M.; Rivas, F.; Cole, K. P.; Aversa, R. J.; Gibe, R.; Umezawa, T.; Suzuki, T. J. Am. Chem. Soc. 2008, 130, 7466.
12. Anand, N. K.; Carreira, E. M. J. Am. Chem. Soc. 2001, 123, 9687.
13. Netherton, M. R.; Dai, C.; Neuschütz, K.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 10099.
14. This furan is also readily prepared by benzylation of (hydroxymethyl) furfural. See: Cottier, L.; Descotes, G.; Eymard, L.; Rapp, K. Synthesis 1995, 303.
15. Kobayashi, Y.; Kusakabe, M.; Kitano, Y.; Sato, F. J. Org. Chem. 1988, 53, 1586.
16. 2 modified conditions employed here see: (a) Yang, Z. C.; Zhou, W. S. Tetrahedron Lett. 1995, 36, 5617.
17. (b) Zhou, W. S.; Lu, Z.; Wang, Z. Tetrahedron Lett. 1991, 32, 1467.
18. (c) Wang, Z.; Zhou, W.; Lin, G. Tetrahedron Lett. 1985, 26, 6221.
19. Garcia-Fandino, R.; Aldegunde, M. J.; Codesido, E. M.; Castedo, L.; Granja, J. R. J. Org. Chem. 2005, 70, 8281.
20. Brimble, M. A.; Bryant, C. J. Org. Biomol Chem. 2007, 5, 2858.
21. Marshall, J. A.; Schaaf, G.; Nolting, A. Org. Lett. 2005, 7, 5331.
22. (a) Chan, K.; Cohen, N.; DeNoble, J. P.; Specian, A. C.; Saucy, G. J. Org. Chem. 1976, 41, 3497.
23. (b) Denmark, S. E.; Jones, T. K. J. Org. Chem. 1982, 47, 4595.
24. Cowell, A.; Stille, J. K. J. Am. Chem. Soc. 1980, 102, 4193.
25. Hoye, T. R.; Humpal, P. E.; Jimenez, J. I.; Mayer, M. J.; Tan, L.; Ye, Z. Tetrahedron Lett. 1994, 35, 7517.
26. Ponpipom, M. M.; Hanessian, S. Carbohydr. Res. 1971, 18, 342.
27. For other examples of the use of this reaction in total synthesis see: (a) Das, S.; Abraham, S.; Sinha, S. C. Org. Lett. 2007, 9, 2273.
28. (b) Keaton, K. A.; Phillips, A. J. Org. Lett. 2007, 9, 2717.
29. Brown, C. A.; Coleman, R. A. J. Org. Chem. 1979, 44, 2328.