Stannylfuranones in synthesis: Highly enantioselective preparation of (+)-hamabiwalactone B

Tetrahedron Letters

Volumn 39, Issue 48, 1998, Pages 8901-8904

  Richecœur, Alexandre M E ^a   Sweeney, J B ^a  

^a UNIVERSITY OF READING   (United Kingdom)

Author keywords

2(5H) Furanone; Hamabiwalactone; Litsea Japonica; Stille reaction

Indexed keywords

FURANONE DERIVATIVE; IODINE DERIVATIVE;

ARTICLE; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PLANT ROOT; STEREOCHEMISTRY; SYNTHESIS;

JAPONICA; LITSEA JAPONICA;

EID: 0032569818     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01946-7     Document Type: Article

References (16)

1. [1] P.G. Marshal, in 'Rodd's Chemistry of Carbon Compounds', 2nd. ed., Elsevier, New York, 1970, Vol. II, Part D, p. 369; D.W. Knight, Contemporary Organic Synthesis, 1994, 1, 287
2. [1] P.G. Marshal, in 'Rodd's Chemistry of Carbon Compounds', 2nd. ed., Elsevier, New York, 1970, Vol. II, Part D, p. 369; D.W. Knight, Contemporary Organic Synthesis, 1994, 1, 287
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7. [5] Previously prepared as an E/Z-mixture: H.J. Bestmann, H.C. Rippel, R. Dostalek, Tetrahedron Lett., 1989, 30, 5261.
8. [6] Previously prepared less efficiently: S.K Taylor, JA Hopkins, K.A. Spangenberg, D.W. Millen, J.B. Grutzner, J. Org. Chem., 1991, 56, 5951.
9. [7] E.J. Corey, P.L. Fuchs, Tetrahedron Lett., 1972, 14, 3769.
10. 2Sn requires 331.0720. 270 (70), 216 (43), 176 (20)
11. 2S requires 206.0402)
12. [10] J. Nokami, T. Ono, Y. Kajitani, S. Wakabayashi, Chem. Lett., 1984, 707; K. Iwai, M. Kawai, H. Kosugi, H. Uda, Chem. Lett., 1974, 385.
13. [10] J. Nokami, T. Ono, Y. Kajitani, S. Wakabayashi, Chem. Lett., 1984, 707; K. Iwai, M. Kawai, H. Kosugi, H. Uda, Chem. Lett., 1974, 385.
14. 2 requires 262.1930), 217 (6), 150 (10), 137 (30), 93 (58)
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16. [13] Column: Chiralcel OB (25cm×4.6mm); Mobile Phase: Hexane/ isopropyl alcohol (90:10); Detector: UV λ. 250nm , Ab 0.64 Å; Flow: 2ml/ min; Load: 10μl of 1mg/ml solution in mobile phase.