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A Model Study toward the Synthesis of Xestoquinone
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 Title & Authors
A Model Study toward the Synthesis of Xestoquinone
Ahn Chan Mug; Ho Bum Woo;
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 Abstract
A strategy for synthesis of the furan-fused tetracyclic system of xestoquinone was explored through a model study. Using 3-butyn-1-ol as a starting material, 5-iodo-1-methoxymethoxy pentyne (5) was prepared in 5 steps. Reaction of ethyl 2-phenylpropanoate with 5 gave ethyl 7-methoxymethoxy-2-methyl-2-phenyl-5-heptynoate (6) in 88% yield, and then methyl 9-oxo-4-methyl-4-phenyl-2,7-nonadiynoate (13), the key intermediate, was synthesized in 6 steps from the ester 6. Intramolecular cycloaddition reaction of 13 afforded isobenzofuran 14 in 5% yield, which was converted to the tetracyclic structure 15 in the presence of Lewis acid.
 Keywords
Xestoguinone;Intramolecular;Cycloaddition;
 Language
Korean
 Cited by
1.
Strategies for the Synthesis of the Halenaquinol and Xestoquinol Families of Natural Products, European Journal of Organic Chemistry, 2017, 2017, 12, 1567  crossref(new windwow)
 References
1.
Deborah, M. R.; Scheuer, P. J. J. Am. Chem. Soc. 1983, 105, 6177. crossref(new window)

2.
Kobayashi, M.; Shimizu, N.; Kyogoku, Y.; Kitagawa, I. Chem. Pharm. Bull. 1985, 33(3), 1305. crossref(new window)

3.
Nakamura, H.; Kobayashi, J.; Kobayashi, M.; Ohizumi, Y.; Hirata, Y. Chem. Lett., 1985, 713. crossref(new window)

4.
Kobayashi, M.; Nakamura, H.; Kobayashi, J.; Ohizumi, Y. J. Pharmacol. Exp. Ther. 1990, 257, 82. crossref(new window)

5.
Kobayashi, M.; Muroyama, A.; Nakamura, H.; Kobayashi, J.; Ohizumi, Y. J. Pharmacol. Exp. Ther. 1990, 257, 90. crossref(new window)

6.
Sakamoto, H.; Furukawa, K.; Matsunaga, K.; Nakamura, H.; Ohizumi, Y. Biochemistry, 1995, 34, 12570. crossref(new window)

7.
Lee, R. H.; Slate, D. L.; Moretti, R.; Alvi, K. A.; Crews P. Biochem. Biophys.Res. Commun. 1992, 184(2), 765. crossref(new window)

8.
Alvi, K.; Rodriguez, J.; Diaz, M. C.; Moretti, R.; William, R. S.; Lee, R. H.; Slate, D. L.; Crews, P. J. Org. Chem. 1993, 58, 4871. crossref(new window)

9.
Harada, N.; Sugioka, T.; Ando, Y.; Uda, H.; Kuriki, T. J. Am. Chem. Soc. 1988, 110, 8483. crossref(new window)

10.
Harada, N.; Sugioka T.; Uda, H.; Kuriki, T. J. Org. Chem. 1990, 55, 3158. crossref(new window)

11.
Kanematsu, K.; Soejima, S.; Wang, G., Tetrahedron Lett. 1991, 32, 4761. crossref(new window)

12.
Kojima, A.; Takemoto, T.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1996, 61, 4876. crossref(new window)

13.
Miyazaki, F.; Uotsu, K.; Shibasaki, M.; Tetrahedron 1998, 54, 13073. crossref(new window)

14.
Carlini, R.; Higgs, K.; Older, C.; Randhawa, S. J. Org. Chem. 1997, 62, 2330. crossref(new window)

15.
Sutherland, H. S.; Souza, F. E. S.; Rodrigo, R. G. A. J. Org. Chem. 2001, 66, 3639. crossref(new window)

16.
Sutherland, H. S.; Higgs, K. C.; Taylor, N. J.; Rodrigo, R. Tetrahedron, 2001, 57, 309. crossref(new window)

17.
Toyooka, N.; Nagaoka, M.; Sasaki, E.; Qin, H.; Kakuda, H.; Nemoto, H. Tetrahedron, 2002, 58, 6097. crossref(new window)

18.
Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277. crossref(new window)

19.
Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 36, 3769. crossref(new window)

20.
Wills, M. S. B.; Danheiser, R. L. J. Am. Chem. Soc. 1998, 120, 9378. crossref(new window)