Pd-catalyzed stereocontrolled synthesis of γ-alkylidenebutenolide, freelingyne

Tetrahedron Letters

Volumn 38, Issue 30, 1997, Pages 5311-5312

  Mori, Hajime ^a   Kubo, Hiroaki ^a   Hara, Hirokazu ^a   Katsumura, Shigeo ^a  

^a KWANSEI GAKUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM; SESQUITERPENOID;

ARTICLE; CATALYST; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0030877830     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01187-8     Document Type: Article

References (12)

1. This work was reported at the 72th Annual Meeting of Chemical Society of Japan, March 27, 1997(Tokyo).
2. Massey-Westropp, R. A.; Reynolds, G. D.; Spotswood, T. K. Tetrahedron, 1966, 18, 1939.
3. a) Pattenden, G.; Knight, D. W. J. Chem. Soc., Perkin Trans. I, 1975, 641.
4. b) Ingram, C. F.; Massey-Westropp, R. A.; Reynolds, G. D. Aust. J. Chem., 1974, 27, 1477.
5. 3CN, which lactonization was originally reported by Lu et al.; a) Kotora, M.; Negishi, E. Tetrahedron Lett., 1996, 37, 9041.
6. b) Lu, X.; Huang, X.; Ma, S. Tetrahedron Lett., 1993, 34, 5963.
7. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett., 1972, 3769.
8. Bieber, P. Ann. Chem., 1954, 9, 674.
9. Duboudin, J. G.; Jousseaume, B. J. Organomet. Chem., 1979, 168, 227.
10. Alami, M.; Ferri, F.; Linstrumelle, G. Tetrahedron Lett., 1993, 34, 6403.
11. Lu et al. originally reported the one-pot construction of γ-alkylidenbutenolide from 3-(Z)-halo-unsaturated carboxylic acids and terminal acetylene compounds. In our case, the preparation of the corresponding carboxylic acid of 7 was not easy and we did not try the one-pot procedure.
12. Quite recently, Negishi et al. have reported their further study of the intramolecular lactonization including the one-pot construction of β-phenyl-substituted γ-alkylidenebutenolides; Kotora, M.; Negishi, E. Synthesis, 1997, 121.