From sugar lactones to stereodefined γ-alkylidenebutenolides - Synthesis of analogs of the γ-alkylidenebutenolide antibiotics lissoclinolide and tetrenolin

European Journal of Organic Chemistry

Volumn , Issue 6, 1998, Pages 1055-1062

  Görth, Felix Christian ^a   Umland, Andreas ^a,b   Brückner, Reinhard ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b Grundstucks Infrastruktur E   (Germany)

Author keywords

C,C Coupling reactions, Pd catalyzed; Eliminations, stereoselective ; Enol triflates; Lactones; Olefins, stereoselective synthesis of

Indexed keywords

EID: 0037682997     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199806)1998:6<1055::aid-ejoc1055>3.0.co;2-m     Document Type: Article

References (38)

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23. Strategically different routes to sterically homogeneous γ-alkylidenebutenolides appear to be limited to the Z-butenolides. Kinetically controlled Z selectivities were reported for mercurylactonizations of ynoic carboxylic acids (M. Yamamoto, J. Chem. Soc. Perkin Trans. 1, 1981, 582-587), iodolactonizations of allenyl carboxylic acids (S. Tsuboi, H Wada, S. Mimiira, A. Takeda, Chem. Lett. 1987, 937-938), and Pd(II)-catalyzed lactonizations of ynoic carboxylic acids (X. Lu, X. Huang, S. Ma, Tetrahedron Lett 1993, 34, 5963-5966; M. Kotora, E.-i. Negishi, Synthesis 1997, 121-128; H. Mori, H. Kubo, H. Hara, S. Katsumura, Tetrahedron Lett. 1997, 38, 5311-5312; F. Liu, E.-i. Negishi, 9th IUPAC Symposium on Organometallic Chemistry Directed Towards Organic Synthesis, Göttingen, Germany, July 20-25, 1997, poster 161).
24. Strategically different routes to sterically homogeneous γ-alkylidenebutenolides appear to be limited to the Z-butenolides. Kinetically controlled Z selectivities were reported for mercurylactonizations of ynoic carboxylic acids (M. Yamamoto, J. Chem. Soc. Perkin Trans. 1, 1981, 582-587), iodolactonizations of allenyl carboxylic acids (S. Tsuboi, H Wada, S. Mimiira, A. Takeda, Chem. Lett. 1987, 937-938), and Pd(II)-catalyzed lactonizations of ynoic carboxylic acids (X. Lu, X. Huang, S. Ma, Tetrahedron Lett 1993, 34, 5963-5966; M. Kotora, E.-i. Negishi, Synthesis 1997, 121-128; H. Mori, H. Kubo, H. Hara, S. Katsumura, Tetrahedron Lett. 1997, 38, 5311-5312; F. Liu, E.-i. Negishi, 9th IUPAC Symposium on Organometallic Chemistry Directed Towards Organic Synthesis, Göttingen, Germany, July 20-25, 1997, poster 161).
25. Strategically different routes to sterically homogeneous γ-alkylidenebutenolides appear to be limited to the Z-butenolides. Kinetically controlled Z selectivities were reported for mercurylactonizations of ynoic carboxylic acids (M. Yamamoto, J. Chem. Soc. Perkin Trans. 1, 1981, 582-587), iodolactonizations of allenyl carboxylic acids (S. Tsuboi, H Wada, S. Mimiira, A. Takeda, Chem. Lett. 1987, 937-938), and Pd(II)-catalyzed lactonizations of ynoic carboxylic acids (X. Lu, X. Huang, S. Ma, Tetrahedron Lett 1993, 34, 5963-5966; M. Kotora, E.-i. Negishi, Synthesis 1997, 121-128; H. Mori, H. Kubo, H. Hara, S. Katsumura, Tetrahedron Lett. 1997, 38, 5311-5312; F. Liu, E.-i. Negishi, 9th IUPAC Symposium on Organometallic Chemistry Directed Towards Organic Synthesis, Göttingen, Germany, July 20-25, 1997, poster 161).
26. Strategically different routes to sterically homogeneous γ-alkylidenebutenolides appear to be limited to the Z-butenolides. Kinetically controlled Z selectivities were reported for mercurylactonizations of ynoic carboxylic acids (M. Yamamoto, J. Chem. Soc. Perkin Trans. 1, 1981, 582-587), iodolactonizations of allenyl carboxylic acids (S. Tsuboi, H Wada, S. Mimiira, A. Takeda, Chem. Lett. 1987, 937-938), and Pd(II)-catalyzed lactonizations of ynoic carboxylic acids (X. Lu, X. Huang, S. Ma, Tetrahedron Lett 1993, 34, 5963-5966; M. Kotora, E.-i. Negishi, Synthesis 1997, 121-128; H. Mori, H. Kubo, H. Hara, S. Katsumura, Tetrahedron Lett. 1997, 38, 5311-5312; F. Liu, E.-i. Negishi, 9th IUPAC Symposium on Organometallic Chemistry Directed Towards Organic Synthesis, Göttingen, Germany, July 20-25, 1997, poster 161).
27. Strategically different routes to sterically homogeneous γ-alkylidenebutenolides appear to be limited to the Z-butenolides. Kinetically controlled Z selectivities were reported for mercurylactonizations of ynoic carboxylic acids (M. Yamamoto, J. Chem. Soc. Perkin Trans. 1, 1981, 582-587), iodolactonizations of allenyl carboxylic acids (S. Tsuboi, H Wada, S. Mimiira, A. Takeda, Chem. Lett. 1987, 937-938), and Pd(II)-catalyzed lactonizations of ynoic carboxylic acids (X. Lu, X. Huang, S. Ma, Tetrahedron Lett 1993, 34, 5963-5966; M. Kotora, E.-i. Negishi, Synthesis 1997, 121-128; H. Mori, H. Kubo, H. Hara, S. Katsumura, Tetrahedron Lett. 1997, 38, 5311-5312; F. Liu, E.-i. Negishi, 9th IUPAC Symposium on Organometallic Chemistry Directed Towards Organic Synthesis, Göttingen, Germany, July 20-25, 1997, poster 161).
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