Concise entry to chiral 5-(4-Hydroxybutyl)-2(5 H)-furanone via HTIB-mediated novel oxidative fragmentation: Formal total synthesis of (+)-dubiusamine A

Organic Letters

Volumn 15, Issue 7, 2013, Pages 1788-1790

  Kawasumi, Muneo ^a   Iwabuchi, Yoshiharu ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DUBIUSAMINE A; FURAN DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; PINE; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; FURANS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PINUS; STEREOISOMERISM;

EID: 84875944770     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol4005239     Document Type: Article

References (34)

1. Wirth, T., Ed. Hypervalent Iodine Chemistry: Modern Developments in Organic Synthesis; Topics in Current Chemistry Series 224; Springer: Berlin, 2003.
2. Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, 1997.
3. Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299
4. Zhdankin, V. V.; Stang, P. Chem. Rev. 2002, 102, 2523
5. Wirth, T. Angew. Chem., Int. Ed. 2005, 44, 3656
6. Silva, L. F., Jr.; Oloff, B. Nat. Prod. Rep. 2011, 28, 1722
7. Moriary, R. M.; Vaid, R. K.; Koser, G. F. Synlett 1990, 365
8. Koser, G. F. Aldrichimica 2001, 34, 89
9. Nabana, T.; Togo, H. J. Org. Chem. 2002, 67, 4362
10. Ueno, M.; Nabana, T.; Togo, H. J. Org. Chem. 2003, 68, 6424
11. Yamamoto, Y.; Togo, H. Synlett 2006, 798
12. Yamamoto, Y.; Kawano, Y.; Toy, P. H.; Togo, H. Tetrahedron 2007, 63, 4680
13. Akiike, J.; Yamamoto, Y.; Togo, H. Synlett 2007, 2168
14. Kawasumi, M.; Kanoh, N.; Iwabuchi, Y. Org. Lett. 2011, 13, 3620
15. Merritt, E. A.; Olofsson, B. Synthesis 2011, 517
16. Staben, S. T.; Linghu, X.; Toste, F. D. J. Am. Chem. Soc. 2006, 128, 12658
17. Tan, M. A.; Kitajima, M.; Kogure, N.; Nonato, M. G.; Takayama, H. Tetrahedron 2010, 66, 3353
18. Nonato, M. G.; Takayama, H.; Garson, M. J. Chapter 4 in The Alkaloids; Cordell, G. A., Ed.; Academic: New York, 2008; Vol. 66, 215.
19. Lim, T. K. Edible Medicinal and Non-Medicinal Plants: Vol. 4, Fruits; Springer: Netherlands, 2012.
20. 2: Suginome, H.; Yamada, S. J. Org. Chem. 1985, 50, 2489
21. Tetrahedron 1987, 43, 3371.
22. Fuhrer, H.; Lorenc, L.; Pavlovic, V.; Rihs, G.; Rist, G.; Kalvoda, J.; Mihailovic, M. Lj. Helv. Chim. Acta 1981, 64, 703
23. Freire, R.; Marrero, J. J.; Rodríguez, M. S.; Suárez, E. Tetrahedron Lett. 1986, 27, 383
24. Arrmas, P.; Francisco, C. G.; Suárez, E. Tetrahedron Lett. 1993, 34, 7331
25. Schreiber, S. L. J. Am. Chem. Soc. 1980, 102, 6163
26. Nakatani, K.; Isoe, S. Tetrahedron Lett. 1984, 25, 5335
27. Heiba, E. I.; Dessau, R. M. J. Am. Chem. Soc. 1971, 93, 524
28. Rigby, J. H.; Psyn, A.; Warshakoon, N. Tetrahedron Lett. 2001, 42, 2047
29. Bandichhor, R.; Nosse, B.; Reiser, O. Top. Curr. Chem. 2005, 243, 43
30. Kitson, R. R. A.; Millemaggi, A.; Taylor, R. J. K. Angew. Chem., Int. Ed. 2009, 48, 9426
31. Devalankar, D. A.; Chouthaiwale, P. V.; Sudalai, A. Tetrahedron; Asymmetry 2012, 23, 240
32. Wu, Y.; Singh, R. P.; Li, D. J. Am. Chem. Soc. 2011, 133, 12458
33. Mao, B.; Geurts, K.; Fananás-Mastral, M.; van Zijl, A. W.; Fletcher, S. P.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2011, 13, 948
34. Kan, T.; Fukuyama, T. Chem. Commun. 2004, 353