Synthetic studies on basidifferquinones: the first synthesis of (±)-basidifferquinone C

Tetrahedron Letters

Volumn 49, Issue 14, 2008, Pages 2258-2261

  Takikawa, Hirosato ^a   Hashimoto, Takashi ^a   Matsuura, Mayuko ^a   Tashiro, Takuya ^b   Kitahara, Takeshi ^c   Mori, Kenji ^b   Sasaki, Mitsuru ^a  

^a KOBE UNIVERSITY   (Japan)

^b RIKEN   (Japan)

^c KITASATO INSTITUTE   (Japan)

Author keywords

Anthraquinones; Diels Alder reaction; Fruiting body inducer; Polyporus arcularius

Indexed keywords

3,5 DIHYDROXY 2 NAPHTHOIC ACID; ACID; BASIDIFFERQUINONE C; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; FRUITING BODY; METHODOLOGY; POLYPORUS; STREPTOMYCES; SYNTHESIS;

ALNUS; POLYPORUS ARCULARIUS; STREPTOMYCES SP.;

EID: 40049098156     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.02.011     Document Type: Article

References (30)

1. (a) For examples: I. Uno T. Ishikawa J. Bacteriol. 113 1973 1240 1248
2. (b) G. Kawai Y. Ikeda Biochim. Biophys. Acta 719 1982 612 618
3. (c) S. Murao H. Hayashi N. Tarui Agric. Biol. Chem. 48 1984 1669 1671
4. (d) H. Hayashi N. Tarui S. Murao Agric. Biol. Chem. 49 1985 101 105
5. (e) Y. Magae T. Nishimura S. Ohara Mycol. Res. 109 2004 374 376
6. (f) Y. Magae S. Ohara Biosci. Biotechnol. Biochem. 70 2006 1979 1982
7. (a) M. Azuma M. Yoshida S. Horinouchi T. Beppu Agric. Biol. Chem. 54 1990 1441 1446
8. (b) M. Azuma K. Hori Y. O-hashi M. Yoshida S. Horinouchi T. Beppu Agric. Biol. Chem. 54 1990 1447 1452
9. M. Azuma M. Yoshida S. Horinouchi T. Beppu Biosci. Biotechnol. Biochem. 57 1993 344 345
10. L. Vertesy M. Kurz E.F. Paulus D. Schummer P. Hammann J. Antibiot. 54 2001 354 363
11. (a) F. Kaiser L. Schwink J. Velder H.-G. Schmalz J. Org. Chem. 67 2002 9248 9256
12. (b) F. Kaiser L. Schwink J. Velder H.-G. Schmalz Tetrahedron 59 2003 3201 3217
13. (c) K. Krohn J. Diederichs M. Riaz Tetrahedron 62 2006 1223 1230
14. (d) D. Sucunza D. Dembkowski S. Neufeind J. Velder J. Lex H.-G. Schmalz Synlett 2007 2569 2573
15. (e) T.S. Lee A. Das C. Khosla Bioorg. Med. Chem. 15 2007 5207 5218
16. These results are unpublished.
17. V. Snieckus Chem. Rev. 90 1990 879 933 and references cited there in
18. (a) S. Danishefsky T. Kitahara J. Am. Chem. Soc. 96 1974 7807 7809
19. (b) S. Danishefsky Acc. Chem. Res. 14 1981 400 406
20. L.F. Tietze C. Güntner K.M. Gericke I. Schuberth G. Bunkoczi Eur. J. Org. Chem. 2005 2459 2467
21. W.D. Wulff W.E. Bauta R.W. Kaesler P.J. Lankford R.A. Miller C.K. Murray D.C. Yang J. Am. Chem. Soc. 112 1990 2642 3659
22. (a) For Lewis acid-mediated Diels–Alder reaction: P. Yates P. Eaton J. Am. Chem. Soc. 82 1960 4436 4437
23. (b) W. Oppolzer B.M. Trost I. Flemming L.A. Paquette Comprehensive Organic Synthesis Vol. 5 1991 Pergamon Oxford 339 345
24. (c) K.C. Nicolaou S.A. Snyder T. Montagnon G. Vassilikogiannakis Angew. Chem., Int. Ed. 41 2002 1668 1698
25. (a) For examples: R.A. Dickinson R. Kubela G.A. MacAlpine Z. Stojanac Z. Valenta Can. J. Chem. 50 1972 2377 2380
26. (b) R.K. Beckman T.M. Dolak K.O. Culos J. Am. Chem. Soc. 100 1978 7098 7100
27. (c) J. Das R. Kubela G.A. MacAlpine Z. Stojanac Z. Valenta Can. J. Chem. 57 1979 3308 3319
28. (d) J.S. Tou W. Reusch J. Org. Chem. 45 1980 5012 5014
29. (e) S. Arséniyadis R. Rodriguez R. Spanevello J. Camara A. Thompson E. Guittet G. Ourisson Tetrahedron 48 1992 1255 1262
30. (f) M.C. Carreño J.L.G. Ruano C.Z. Remor A. Urbano Tetrahedron: Asymmetry 11 2000 4279 4296