Synthesis of the core framework of the proposed structure of sargafuran

Tetrahedron Letters

Volumn 54, Issue 4, 2013, Pages 347-350

  Katsuta, Ryo ^a   Aoki, Kazuya ^a   Yajima, Arata ^a   Nukada, Tomoo ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE   (Japan)

Author keywords

Cyclopentadienol; Furan; Natural products; Sargafuran; Synthesis

Indexed keywords

2 HOMOPRENYL 1 METHYL 3 (5 METHYLFURAN 2 YL)CYCLOPENTA 2,4 DIEN 1 OL; FURAN DERIVATIVE; METHANOL; UNCLASSIFIED DRUG;

ARTICLE; BROWN ALGA; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; PIANCATELLI REARRANGEMENT; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION;

PHAEOPHYCEAE;

EID: 84871623807     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.11.052     Document Type: Article

References (21)

1. T. Kikuchi, Y. Mori, T. Yokoi, S. Nakazawa, H. Kuroda, Y. Masada, K. Kitamura, and I. Umezaki Chem. Pharm. Bull. 23 1975 690 692
2. T. Kikuchi, Y. Mori, T. Yokoi, S. Nakazawa, H. Kuroda, Y. Masada, K. Kitamura, and K. Kuriyama Chem. Pharm. Bull. 31 1983 106 113
3. T. Kusumi, Y. Shibata, M. Ishitsuka, T. Kinoshita, and H. Kakisawa Chem. Lett. 1979 277 278
4. Y. Seo, K.E. Park, and T.J. Nam Bull. Korean Chem. Soc. 28 2007 1831 1833
5. M. Segawa, and H. Shirahama Chem. Lett. 1987 1365 1366
6. C.K. Tsang, A. Ina, T. Goto, and Y. Kamei Neuroscience 132 2005 633 643
7. M. Iwashima, J. Mori, X. Ting, T. Matsunaga, K. Hayashi, D. Shinoda, H. Saito, U. Sankawa, and T. Hayashi Biol. Pharm. Bull. 28 2005 374 377
8. P. Reddy, and S. Urban Phytochemistry 70 2009 250 255
9. Y. Kamei, M. Sueyoshi, K. Hayashi, R. Terada, and H. Nozaki J. Antibiot. 62 2009 259 263
10. H. Urabe, M. Narita, and F. Sato Angew. Chem., Int. Ed. 38 1999 3516 3518
11. L.G. Quan, V. Gevorgyan, and Y. Yamamoto J. Am. Chem. Soc. 121 1999 3545 3546
12. G. Piancatelli, and A. Screttri Tetrahedron Lett. 18 1977 1131 1134
13. G. Piancatelli, A. Screttri, G. David, and M. D'Auria Tetrahedron 34 1978 2775 2778
14. I. Dohgane, H. Yamachika, and H. Minai J. Synth. Org. Chem. Jpn. 41 1983 896 903
15. Saito, K.; Yamachika, H. U.S. Patent 4,356,326, 1982.
16. Saito, K.; Yamachika, H. U.S. Patent 4,371,711, 1983.
17. A review of these types of reactions: G. Piancatelli, M. D'Auria, and F. D'Onfrio Synthesis 1994 867 889
18. P. Laszlo, and P. Schleyer J. Am. Chem. Soc. 85 1963 2017 2018
19. V.X. Chen, F.D. Boyer, C. Rameau, P. Retailleau, J.P. Vors, and J.M. Beau Chem. Eur. J. 16 2010 13941 13945
20. M. Kuroda, S. Kubo, S. Uchida, H. Sakagami, and Y. Mimaki Steroids 75 2010 83 94
21. N. Galy, D. Moraleda, and M. Santelli Tetrahedron Lett. 50 2009 5238 5240