Synthesis and biological evaluation of the four racemic stereoisomers of the structure proposed for sorgolactone, the germination stimulant from Sorghum bicolor

Tetrahedron Letters

Volumn 38, Issue 14, 1997, Pages 2507-2510

  Mori, Kenji ^a   Matsui, Junichi ^a   Bando, Masahiko ^b   Kido, Masaru ^b   Takeuchi, Yasutomo ^c  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

^b OTSUKA PHARMACEUTICAL CO LTD   (Japan)

^c UTSUNOMIYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE DERIVATIVE; SORGOLACTONE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; GERMINATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; X RAY ANALYSIS;

EID: 0030957586     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00379-1     Document Type: Article

References (23)

1. Parker, C.; Riches, C.R. Parasitic Weeds of the World, Biology and Control, CAB International, Willingford, Oxon., U.K., 1993.
2. Sand, P.F.; Eplee, R.E.; Westbrooks, R.G. Witchweed Research and Control in the United States, Weed Science Society of America, 1990.
3. Cook C.E., Whichard L.P., Wall M.E., Egley G.H., Coggon P., Luhan P.A., McPhail A.T. J. Am. Chem. Soc. 94:1972;6198-6199.
4. Siame B.A., Weerasuriya Y., Wood K., Ejeta G., Butler L.G. J. Agric. Food Chem. 41:1993;1486-1491.
5. Heather J.B., Mittal R.S.D., Sih C.J. J. Am. Chem. Soc. 98:1976;3661-3669.
6. MacAlpine G.A., Raphael R.A., Shaw A., Taylor A.W., Wild H.-J. J. Chem. Soc., Perkin Trans. 1:1976;410-416.
7. Brooks D.W., Bevinakatti H.S., Powell D.R. J. Org. Chem. 50:1985;3779-3781.
8. Thuring J.W.J.F., Nefkens G.H.L., Wegman M.A., Klunder A.J.H., Zwanenburg B. J. Org. Chem. 61:1996;6931-6935.
9. Kranz A., Samson-Schulz E., Henning L., Welzel P., Müller D., Mayer-Figge H., Sheldrick W.S. Tetrahedron. 52:1996;14827-14840.
10. Hauck C., Müller S., Schildeknecht H. J. Plant Physiol. 139:1992;474-478.
11. Schröer J., Welzel P. Tetrahedron. 50:1994;6839-6858.
12. Mikló K., Jaszberenyi J.Cs., Kádas I., Árvai G., Tõke L. Tetrahedron Lett. 37:1996;3491-3494.
13. Kádas I., Árvai G., Tõke L., Tóth G., Szöllõsy Á., Bihari M. Tetrahedron. 50:1994;2895-2906.
14. Luche J.-L. J. Am. Chem. Soc. 100:1978;2226-2227.
15. All the new compounds were characterized by spectroscopic (IR and NMR) and elemental (combustion or HRMS) analyses.
16. Frischmuth K., Samson E., Kranz A., Welzel P., Meuer H., Sheldrick W.S. Tetrahedron. 47:1991;9793-9806.
17. -1. Of the 1521 independent reflections collected, 840 reflections with I > 3.0σ(I) were used for the structure determination. The final refinement converged with R = 0.056 and Rw = 0.072 for 127 parameters. Atomic coordinates have been deposited at the Cambridge Crystallographic Data Center.
18. -1. Of the 2285 independent reflections collected, 1248 reflections with I > 3.0σ(I) were used for the structure determination. The final refinement converged with R = 0.056 and Rw = 0.063 for 208 parameters. Atomic coordinates have been deposited at the Cambridge Crystallographic Data Center.
19. +), 219, 201, 173, 145, 131, 105, 97, 91.
20. Hauck C., Schildeknecht H. J. Plant Physiol. 136:1990;126-128.
21. Mangnus E.M., Zwanenburg B. J. Agric. Food Chem. 40:1992;697-700.
22. Bergmann C., Wegmann K., Frischmuth K., Samson E., Kranz A., Weigelt D., Koll P., Welzel P. J. Plant Physiol. 142:1993;338-342.
23. Takeuchi Y., Omigawa Y., Ogasawara M., Yoneyama K., Konnai M., Worsham A.D. Plant Growth Regul. 16:1995;153-160.