A. Bieniek et al. / Tetrahedron Letters 42 (2001) 9293–9295
9295
Table 1. Detailed yields (%) of the conversion 18
J.; Masuma, R.; Oiwa, R.; Omura, S. J. Antibiot. 1978,
31, 959.
8. Kulanthaivel, P.; Perun, Jr., T. J.; Belvo, M. D.; Strobel,
R. J.; Paul, D. C.; Williams, D. C. J. Antibiot. 1999, 52,
256.
9. Tsukamoto, M.; Nakajima, S.; Murooka, K.; Hirayama,
M.; Hirano, K.; Yoshida, S.; Kojiri, K.; Suda, H. J.
Antibiot. 2000, 53, 26.
13
35
57
78
a
b
c
68
67
75
68
94
88
92
96
74
70
72
68
81
80
83
80
d
10. Tsukamoto, M.; Nakajima, S.; Murooka, K.; Naito, M.;
Suzuki, H.; Hirayama, M.; Hirano, K.; Kojiri, K.; Suda,
H. J. Antibiot. 2000, 53, 687.
11. Tatsuta, K.; Akimoto, K.; Annako, M.; Ohno, Y.;
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Chem. Soc. 1989, 111, 989.
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14. Brunble, M. A.; Stuart, S. J. J. Chem. Soc., Perkin Trans.
1 1990, 881.
are trans isomers (C-e/e). The coupling constant of the
hydrogen atoms (C-a/a) ranged between 6.4 and 9.2
Hz.35 The structure of the isochromans 8, exemplified
by compound 8c was confirmed by X-ray crystallogra-
phy.29 The formation of the trans isomers is most
probably due to the fact that the approach trajectory of
the incoming nucleophile, is opposite to the aryl sub-
stituents of the oxonium cation generated from the
3-hydroxy-4-arylisochromans (7).
15. Trost, B. Chem. Rev. 1978, 78, 363.
16. Mosquelin, T.; Hengartner, U.; Streith, J. Synthesis 1995,
780.
Overall yields for the regio- and diastereotransforma-
tion of the starting benzoic acid anilides (1) into ben-
zo[c]pyran-3-acetic acids methyl esters (8) are about
40% (Table 1).
17. Mosquelin, T.; Hengartner, U.; Streith, J. Helv. Chim.
Acta 1997, 80, 43.
18. Cantant, P.; Haess, M.; Riegl, J.; Scalone, M.; Visnick,
M. Synthesis 1999, 821.
19. Epsztajn, J.; Bieniek, A.; Kowalska, J. A. Tetrahedron
In conclusion, we have shown a novel general strategy
for the preparation of the 3,4-disubstituted isochro-
mans. The procedure is particularly useful because of
its efficiency, ready availability of the starting materials
and ease of operation, as well as its applicability to the
synthesis of important natural products.
1991, 47, 1697.
20. Epsztajn, J.; Bieniek, A.; Kowalska, J. A.; Scianowski, J.
Monatsh. Chem. 1992, 123, 1125.
21. Epsztajn, J.; Bieniek, A.; Kowalska, J. A. Monatsh.
Chem. 1996, 127, 701.
22. Epsztajn, J.; Bieniek, A.; Kowalska, J. A.; Kulikiewicz,
K. K. Synthesis 2000, 1603.
23. Adams, R.; Hartenist, M.; Loeve, S. J. Am. Chem. Soc.
Acknowledgements
1949, 71, 1624.
24. Takahashi, T.; Jkeda, H.; Tsuji, J. Tetrahedron Lett.
1980, 21, 3885.
25. Azzena, U.; Demartis, S.; Fiori, M. G.; Melloni, G.;
Pisano, L. Tetrahedron Lett. 1995, 36, 8123.
26. Azzena, U.; Demartis, S.; Hellani, G. J. Org. Chem. 1996,
61, 4913.
This work was supported by Grant-in-Aid for Scientific
Research from the State Committee for Scientific
Research (KBN), and is gratefully acknowledged.
27. Yus, M.; Foubelo, F. Rev. Heteroatom Chem. 1997, 17,
73.
28. Ramon, D. J.; Yus, M. Eur. J. Org. Chem. 2000, 225.
29. The X-ray data for compounds 7 and 8 will be described
elsewhere.
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