Abstract
A facile single-step synthesis of the title isocoumarins isolated from Xyris indica has been elaborated. Condensation of butanoyl chloride and 2-oxobutanoyl chloride with 3,4-methylenedioxyhomophthalic acid afforded xyridin A and xyridin B, respectively. Xyridin A was saponified to the corresponding keto acid, which on reduction gave the (±)-3,4-dihydro-6,7-methylenedioxy-3-propylisocoumarin in which diastereotopy of the methylenic protons around the stereogenic center was observed. A mass fragmentation mechanism for xyridins has also been suggested.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
N. Ruangrungsi, T. Sekine, T. Phadungcharoen, S. Suriyagan, and I. Murakoshi, Phytochemistry, 38, 481 (1995).
V. H. Belgaonkar and R. N. Usgaonkar, J. Chem. Soc., Perkin Trans. 1, 702 (1977).
J. N. Srivasta and D. N. Chaudhury, J. Org. Chem., 27, 4337 (1962).
B. H. Bhide and K. K. Shah, Indian J. Chem., 19B, 9 (1980).
J. Katakawa, H. Meguri, and H. Irie, Heterocycles, 22, 2213 (1984).
R. C. Thompson and J. Kallmerten, J. Org. Chem., 55, 6076 (1990).
H. Paulsen and M. Stubbe, Liebigs Ann. Chem., 535 (1983).
T. K. Park and S. J. Danishefsky, Tetrahedron Lett., 36, 195 (1995).
G. E. Keck, S. F. McHardy and J. A. Murry, J. Am. Chem. Soc., 117, 7289 (1995).
M. M. Abelman, L. E. Overman and V. D. Tran, J. Am. Chem. Soc., 112, 6959 (1990).
J. J. Fitzgerald, A. R. Pagano, V. M. Sakoda and R. A. Olofson, J. Org. Chem., 59, 4117 (1994).
N. H. Rama, A. Saeed and C. W. Bird, Liebigs Ann. Chem., 1331 (1993).
N. H. Rama, A. Saeed and C. W. Bird, Liebigs Ann. Chem., 711 (1995).
A. Saeed and N. H. Rama, J. Chem. Soc. Pak., 16, 220 (1994).
A. Saeed and N. H. Rama, Arabian J. Sci. Eng., 21, 403 (1996).
N. H. Rama, R. Iqbal, Kh. Zamani, A. Saeed, M. Z. Iqbal, and M. I. Chaudary, Indian J. Chem., 37B, 365 (1998).
K. Nozawa, M. Yamada, Y. Tsuda, K. I. Kawai, and S. Nakajima, Chem. Pharm. Bull., 29, 2491 (1981).
K. Nozawa, M. Yamada, Y. Tsuda, K. I. Kawai, and S. Nakajima, Chem. Pharm. Bull., 29, 3486 (1981).
H. Kaji, M. Yamada, K. Nozawa, K. I. Kawai, and S. Nakajima, Org. Prep. Proced. Int., 18, 253 (1986).
T. Kanda, S. Kato, T. Sugino, N. Kambe, A. Oganawa, and N. Sonoda, Synthesis, 1102 (1995).
J. K. Kendall, T. H. Fisher, H. P. Schultz, and T. P. Schultz, J. Org. Chem., 54, 6076 (1989).
D. H. Williams and I. Fleming, Spectroscopic Methods in Organic Chemistry, 4th Ed., McGraw-Hill, UK, 1987, p. 88.
D. Becker, L. R. Hughes, and R. A. Raphael, J. Chem. Soc., Perkin Trans. 1, 1674 (1977).
Author information
Authors and Affiliations
Additional information
__________
Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1140–1145, August, 2005.
Rights and permissions
About this article
Cite this article
Saeed, A. A Single-Step Synthesis of Xyridins A and B, Metabolites from Xyris indica . Chem Heterocycl Compd 41, 967–972 (2005). https://doi.org/10.1007/s10593-005-0262-9
Received:
Issue Date:
DOI: https://doi.org/10.1007/s10593-005-0262-9