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Natural Product Letters Volume 5, 1994 - Issue 2
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Original Articles

Diastereoselective Three-center Michael Addition. Part 2. 1 A New Entry into the Prelog-Djerassi Lactone Framework

Nicole Ouvrard Laboratoire de Synthèse Organique, URA CNRS 1411, Centre de St. Jérome, boǐte D 12, 13397, Marseille cedex 20, France
,
Jean Rodriguez Laboratoire de Synthèse Organique, URA CNRS 1411, Centre de St. Jérome, boǐte D 12, 13397, Marseille cedex 20, France
&
Maurice Santelli Laboratoire de Synthèse Organique, URA CNRS 1411, Centre de St. Jérome, boǐte D 12, 13397, Marseille cedex 20, France
Pages 153-155 | Received 23 Aug 1994, Published online: 04 Oct 2006

References

  • Ouvrard , N. , Rodriguez , J. and Santelli , M. 1992 . Diastereoselective three-center Michael addition of β-ketoesters to prostereogenic α,β-unsaturated carbonyl compounds catalyzed by K2CO3 or Cs2CO3 . Angewandte Chemie International Edition in English , 31 : 1651 – 1653 . Part 1
  • Fuji , K. 1993 . Asymmetric creation of quaternary carbon cenetrs . Chemical Review , 93 : 2037 – 2066 . For an excellent recent review on asymmetric creation of quaternary carbon atoms, see:
  • Martin , S. F. and Guinn , D. E. 1991 . Prelog-Djerassi lactonic acid. A target for design and development of stereoselective synthetic methods . Synthesis , : 245 – 262 . For a recent review, see:
  • Ouvrard , N. , Rodriguez , J. and Santelli , M. 1993 . Stereoselective ester dienolate Carroll rearrangement: a new approach to the Prelog-Djerassi lactone framework . Tetrahedron Letters , 34 : 1149 – 1150 .
  • Sell , C. S. 1975 . Competitive reduction of aldehyde-ketone mixtures by complex hydroborates and hydroaluminates . Australian Journal of Chemistry , 28 : 1383 – 1384 .
  • Sharpless , K. B. and Young , M. W. 1975 . Olefin synthesis. Rate enhancement of the elimination of aryl selenoxides by electron-withdrawing substituents . Journal of Organic Chemistry , 40 : 947 – 949 .
  • Grieco , P. A. , Gilman , S. and Nishizawa , M. 1976 . Organoselenium Chemistry. A facile one-step synthesis of alkyl aryl selenides from alcohols . Journal of Organic Chemistry , 41 : 1485 – 1486 .
  • trans,-12 : colorless oil, Rf ,= 0.42 (diethyl ether-pentane, 1:9); [α]578 26 +109 (c, 0.4 in CHCl3); vmax , (film)/cm−1 2970, 2930, 2860 and 1740; δH(400 MHz; CDCl3) 5.77 (1H, ddd, J, 17.1, 10.3 and 7.5), 4.97 (1H, dt, J, 17.1 and 1.5), 4.95 (1H, ddd, J, 10.3, 1.5 and 1.1), 2.67 (1H, m), 2.25 (1H, m), 2.03 (3H, m), 1.68 (1H, ddd, J, 9.3, 4.0 and 1.5), 1.33 (1H, m), 1.12 (3H, d, J, 6.3) and 1.07 (3H, d, J, 7.1); δC(100 MHz; CDCl3) 220.4, 141.3, 114.4, 61.5, 38.7, 37.1, 33.9, 29.7, 21.1 and 17.5; Anal. Calcd. for C10H16O: C, 78.95; H, 10.53. Found: C, 78.92; H, 10.58

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