Oxindole alkaloids. A novel non-biomimetic entry to (-)-horsfiline

Tetrahedron Asymmetry

Volumn 7, Issue 1, 1996, Pages 1-4

  Palmisano, Giovanni ^a   Annunziata, Rita ^b   Papeo, Gianluca ^b   Sisti, Massimo ^b  

^a UNIVERSITY OF TURIN   (Italy)

^b UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

HORSFILINE; INDOLE ALKALOID; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030032914     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(95)00406-8     Document Type: Article

References (35)

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27. The choice of molecular sieves is crucial and the use of 4Å or 5Å resulted in lower yields and longer reaction times.See: Mikami, T.; Yoshida, A. SYNLETT, 1995, 29-31; Koga, Y.; Sodeoka, M.; Shibasaki, M. Tetrahedon Lett. 1994, 35, 1227- 1230
28. The choice of molecular sieves is crucial and the use of 4Å or 5Å resulted in lower yields and longer reaction times.See: Mikami, T.; Yoshida, A. SYNLETT, 1995, 29-31; Koga, Y.; Sodeoka, M.; Shibasaki, M. Tetrahedon Lett. 1994, 35, 1227-1230
29. 1H NMR of the reaction mixture
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33. Enantiomerically pure 12 was prepared from 7 by Wittig olefination with (5R)-carboxymenthyloxymethylene triphenylphosphorane ( Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W.J. Tetrahedron 1992, 48, 6929-6952)
34. 3), CD λ(Δε) 241(-2.42), 248(0), 260(+2.82), 277(=), 306(-2.32); 1H NMR 0.34 & 0.65(2 × 3H,2 xd,J 7.0, H-9"/H-10"), 0.84(3H,d,J 7.0, H-7"), 2.44(3H,s,NMe), 2.74 & 2.98(AB syst. 2H, J 9.1, H-2'), 3.69(1H,dd; J 8.9, 7.2; H-4"), 3.77(3H, s.OMe), 4.40(1H,dt; J 10.8, 4.4; H-1"); CMR 15.2 & 22.4(C-9"/C-10"), 21.6(C-7"), 40.3(C-6'), 51.8(C-4'), 56.5 & 56.7(C-3/C-5'), 67.0(C-2'), 74.6(C-1"), 109.3 & 111.7(C-4/C-6), 169.6(CO2), 179.2(CON).
35. Several asymmetric examples of 1,3-dipolar cycloaddition of azomethine ylides to electron-deficient alkenes has been reported; see: Pyne, S.G.; Safaei-G., J.; Koller, F. Tetrahedron Lett. 1995, 36, 2511-2514 and references therein.