The first total synthesis of the naturally occurring germination stimulant sorgolactone

Tetrahedron Letters

Volumn 38, Issue 13, 1997, Pages 2321-2324

  Sugimoto, Yukihiro ^a,b   Wigchert, Suzanne C M ^a   Thuring, Jan Willem J F ^a   Zwanenburg, Binne ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

^b TOTTORI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE DERIVATIVE;

ARTICLE; CIRCULAR DICHROISM; DRUG PURITY; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031592582     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00304-3     Document Type: Article

References (14)

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3. c. Samson, E.; Frischmuth, K.; Berlage, U.; Heinz, U.; Hobert, K.; Welzel, P. Tetrahedron 1991, 47, 1411-1416.
4. 2. Brooks, D.W.; Bevinakatti, H.S.; Powell, D.R. J.Org.Chem. 1985, 50, 3779-3781.
5. 3 Hauck, C. Thesis, Ruprecht-Karls Universität, Heidelberg 1990.
6. 4. Hauck, C.; Müller, S.; Schildknecht, H. J.Plant Physiol. 1992, 139, 474-478.
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8. 6. Mangnus, E.M.; Dommerholt, F.J.; de Jong, R.L.P.; Zwanenburg, B. J.Agric.Food Chem. 1992, 40, 1230-1235.
9. 3): δ 19.85; 20.37; 26.24; 30.07; 31.63; 34.72; 36.20; 42.41; 92.60; 136.89; 142.84; 177.76.
10. 3): δ 1.13 (d, 3H, J=7.0Hz, 3xH9); 1.34 (m, 1H, H7); 1.54 (m, 1H, H6); 1.72 (m, 2H, H6+H7); 1.98 (m, 2H. 2xH5); 2.03 (s, 3H, 3xH7′); 2.31 (m, 1H, H8); 2.33 (bd, 1H, J=16.9Hz, H4); 2.71 (ddd, 1H, J=3.1Hz, 9.2Hz, 16.8Hz, H4); 3.62 (m, 1H, H3a); 5.35 (d, 1H, J=7.6Hz, H8b); 6.15 (s, 1H, H2′); 6.92 (s, 1H, H3′); 7.42 (d, 1H, J=2.5Hz, H6′).
11. 9. a. Thuring, J.W.J.F.; Nefkens, G.H.L.; Schaafstra, R.; Zwanenburg, B. Tetrahedron 1995, 51, 5047-5056.
12. b) Thuring, J.W.J.F.; Nefkens, G.H.L.; Wegman, M.A.; Klunder, A.J.H.; Zwanenburg, B. J.Org.Chem. 1996, 61, 6931-6935.
13. max=230nm, Δε=20.
14. 11. Thuring, J.W.J.F.; Heinsman, N.W.J.T.; Jacobs, R.W.A.W.M.; Nefkens, G.H.L.; Zwanenburg, B. J.Agric.Food Chem. 1996 accepted for publication