Preparation of (+)-Hamabiwalactone B via Stille coupling of an enantiomerically pure stannylfuranone

Tetrahedron

Volumn 56, Issue 3, 2000, Pages 389-395

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

^a UNIVERSITY OF READING   (United Kingdom)

^b UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

(+) Hamabiwalactone B; Enantioselective synthesis; Stille coupling

Indexed keywords

FURANONE DERIVATIVE; HAMABIWALACTONE; LACTONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0037847353     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/s0040-4020(99)00998-9     Document Type: Article

References (19)

1. Marshal, P. G. In Rodd's Chemistry of Carbon Compounds, 2nd ed.; Elsevier: New York, 1970; Vol. II, Part D, p 369; Knight, D. W. Contemporary Organic Synthesis 1994, 1, 287.
2. Marshal, P. G. In Rodd's Chemistry of Carbon Compounds, 2nd ed.; Elsevier: New York, 1970; Vol. II, Part D, p 369; Knight, D. W. Contemporary Organic Synthesis 1994, 1, 287.
3. Hollingworth, G. J.; Perkins, G.; Sweeney, J. B. J. Chem. Soc., Perkin Trans. 1 1996, 1913; Hollingworth, G. J.; Richecœur, A. M. E.; Sweeney, J. B. J. Chem. Soc., Perkin Trans. 1 1996, 2833.
4. Hollingworth, G. J.; Perkins, G.; Sweeney, J. B. J. Chem. Soc., Perkin Trans. 1 1996, 1913; Hollingworth, G. J.; Richecœur, A. M. E.; Sweeney, J. B. J. Chem. Soc., Perkin Trans. 1 1996, 2833.
5. Richecœur, A. M. E.; Sweeney, J. B. Tetrahedron Lett. 1998, 39, 8901.
6. Tanaka, H.; Nakamura, T.; Ichino, K.; Ito, K.; Tanaka, T. Phytochemistry 1990, 29, 857.
7. Iwai, K.; Kosogi, H.; Uda, H.; Kawai, M. Bull. Chem. Soc. Jpn. 1977, 50, 242.
8. Bestmann, H. J.; Rippel, H. C.; Dostalek, R. Tetrahedron Lett. 1989, 30, 5261.
9. Taylor, S.; Hopkins, J. A.; Spangenberg, K. A.; Millen, D. W.; Grutzner, J. B. J. Org. Chem. 1991, 56, 5951.
10. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 14, 3769.
11. Nokami, J.; Ono, T.; Kajitani, Y.; Wakabayashi, S. Chem. Lett. 1984, 707; Iwai, K.; Kawai, M.; Kosugi, H.; Uda, H. Chem. Lett. 1974, 385.
12. Nokami, J.; Ono, T.; Kajitani, Y.; Wakabayashi, S. Chem. Lett. 1984, 707; Iwai, K.; Kawai, M.; Kosugi, H.; Uda, H. Chem. Lett. 1974, 385.
13. Martinez, J. C.; Yoshida, M.; Gottlieb, O. R.; Phytochemistry 1981, 20, 59; Viera, P. C.; Yoshida, M.; Gottlieb, O. R.; Filho, H. F. P.; Nagem, T. J.; Filho, R. B. Phytochemistry 1983, 22, 711; Ortuno, R. M.; Bigorra, J.; Font, J. Tetrahedron 1988, 44, 5139; Nishide, K.; Aramata, A.; Kamanaka, T.; Inoue, T.; Node, M. Tetrahedron 1994, 28, 8337; Chaves, H. M.; Roque, N. F. Phytochemistry 1997, 44, 523.
14. Martinez, J. C.; Yoshida, M.; Gottlieb, O. R.; Phytochemistry 1981, 20, 59; Viera, P. C.; Yoshida, M.; Gottlieb, O. R.; Filho, H. F. P.; Nagem, T. J.; Filho, R. B. Phytochemistry 1983, 22, 711; Ortuno, R. M.; Bigorra, J.; Font, J. Tetrahedron 1988, 44, 5139; Nishide, K.; Aramata, A.; Kamanaka, T.; Inoue, T.; Node, M. Tetrahedron 1994, 28, 8337; Chaves, H. M.; Roque, N. F. Phytochemistry 1997, 44, 523.
15. Martinez, J. C.; Yoshida, M.; Gottlieb, O. R.; Phytochemistry 1981, 20, 59; Viera, P. C.; Yoshida, M.; Gottlieb, O. R.; Filho, H. F. P.; Nagem, T. J.; Filho, R. B. Phytochemistry 1983, 22, 711; Ortuno, R. M.; Bigorra, J.; Font, J. Tetrahedron 1988, 44, 5139; Nishide, K.; Aramata, A.; Kamanaka, T.; Inoue, T.; Node, M. Tetrahedron 1994, 28, 8337; Chaves, H. M.; Roque, N. F. Phytochemistry 1997, 44, 523.
16. Martinez, J. C.; Yoshida, M.; Gottlieb, O. R.; Phytochemistry 1981, 20, 59; Viera, P. C.; Yoshida, M.; Gottlieb, O. R.; Filho, H. F. P.; Nagem, T. J.; Filho, R. B. Phytochemistry 1983, 22, 711; Ortuno, R. M.; Bigorra, J.; Font, J. Tetrahedron 1988, 44, 5139; Nishide, K.; Aramata, A.; Kamanaka, T.; Inoue, T.; Node, M. Tetrahedron 1994, 28, 8337; Chaves, H. M.; Roque, N. F. Phytochemistry 1997, 44, 523.
17. Martinez, J. C.; Yoshida, M.; Gottlieb, O. R.; Phytochemistry 1981, 20, 59; Viera, P. C.; Yoshida, M.; Gottlieb, O. R.; Filho, H. F. P.; Nagem, T. J.; Filho, R. B. Phytochemistry 1983, 22, 711; Ortuno, R. M.; Bigorra, J.; Font, J. Tetrahedron 1988, 44, 5139; Nishide, K.; Aramata, A.; Kamanaka, T.; Inoue, T.; Node, M. Tetrahedron 1994, 28, 8337; Chaves, H. M.; Roque, N. F. Phytochemistry 1997, 44, 523.
18. Column: Chiralcel OB (25 cm×4.6 mm); Mobile phase: hexane/isopropyl alcohol (90:10); Detector: UV λ 250 nm, Ab 0.64 Å; Flow: 2 ml/min; Load: 10 μl of 1 mg/ml solution in mobile phase.
19. Takeda, K.; Sakurawi, K.; Ishii, H. Tetrahedron 1972, 28, 3757.