Total Synthesis of Prostaglandin F2α via Nickel-Promoted Stereoselective Cyclization of 1,3-Diene and Aldehyde

Synlett

Volumn 1997, Issue 6, 1997, Pages 734-736

  Sato, Yoshihiro ^a   Takimoto, Masanori ^a   Mori, Miwako ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

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[No Author keywords available]

Indexed keywords

EID: 0001495843     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-3268     Document Type: Article

References (29)

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2. For reviews, see: (a) Jolly, P. W. In Comprehensive Organometallic Chemistry; Wilkinson, G.; Stone, F. G. A.; Abel, E. W., Eds.; Pergamon: New York, 1982; Vol. 8, p 613. (b) Keim, W.; Behr, A.; Roper, M. ibid, p 371. (c) Heimback, P. Angew Chem., Int. Ed. Engl. 1973, 12, 975. (d) Wilke, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 185.
3. For reviews, see: (a) Jolly, P. W. In Comprehensive Organometallic Chemistry; Wilkinson, G.; Stone, F. G. A.; Abel, E. W., Eds.; Pergamon: New York, 1982; Vol. 8, p 613. (b) Keim, W.; Behr, A.; Roper, M. ibid, p 371. (c) Heimback, P. Angew Chem., Int. Ed. Engl. 1973, 12, 975. (d) Wilke, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 185.
4. For reviews, see: (a) Jolly, P. W. In Comprehensive Organometallic Chemistry; Wilkinson, G.; Stone, F. G. A.; Abel, E. W., Eds.; Pergamon: New York, 1982; Vol. 8, p 613. (b) Keim, W.; Behr, A.; Roper, M. ibid, p 371. (c) Heimback, P. Angew Chem., Int. Ed. Engl. 1973, 12, 975. (d) Wilke, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 185.
5. (a) For [4+4] cycloadditions, see: Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089 and references cited therein.
6. (b) Tamao, K.; Kobayashi, K.; Ito, Y. Synlett 1992, 539. Tamao, K.; Kobayashi, K.; Ito, Y. J. Synth. Org. Chem. Jpn. 1990, 48, 381.
7. (b) Tamao, K.; Kobayashi, K.; Ito, Y. Synlett 1992, 539. Tamao, K.; Kobayashi, K.; Ito, Y. J. Synth. Org. Chem. Jpn. 1990, 48, 381.
8. (c) For [4+2] cycloadditions, see: Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824 and references cited therein.
9. (d) For nickel-promoted intermolecular reactions of 1,3-diene and carbonyl compound, see: Baker, R.; Cook, A. H.; Crimmin, M. J. J. Chem. Soc. Chem. Commun. 1975, 727. Baker, R.; Crimmin, M. J. J. Chem. Soc. Perkin I 1979, 1264.
10. (d) For nickel-promoted intermolecular reactions of 1,3-diene and carbonyl compound, see: Baker, R.; Cook, A. H.; Crimmin, M. J. J. Chem. Soc. Chem. Commun. 1975, 727. Baker, R.; Crimmin, M. J. J. Chem. Soc. Perkin I 1979, 1264.
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13. (a) Corey, E. J.; Cheng, X.-M. The Logic of Chemical Synthesis; Wiley: New York, 1989; pp 249-309 and references cited therein.
14. (b) Mitra, A. The Synthesis of Prostaglandins; Wiley: New York, 1977.
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17. 2α.
18. 2 at -20 °C.
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22. 2 5) TBAF, THF 64% (5 steps)
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26. 2α with diazomethane, were also completely identical to those reported previously. 16
27. Corey, E. J.; Schaaf, T. K.; Huber, W.; Koelliker, U.; Weinshenker, N. M. J. Am. Chem. Soc. 1970, 92, 397.
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