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Volumn 68, Issue 7, 2003, Pages 2913-2920

Total synthesis of (+)-astrophylline

Author keywords

[No Author keywords available]

Indexed keywords

RING-CLOSING METATHESIS;

EID: 0037419166     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026803h     Document Type: Article
Times cited : (47)

References (41)
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    • For further examples of tandem ring rearrangement (RCM-ROM-RCM) metathesis reactions, see: a) Zuercher, W. J.; Hashimoto, M.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 6634-6640. b) Burke, S. D.; Quinn, K J.; Chen, V. J. J. Org. Chem. 1998, 63, 8626-8627. c) Zuercher, W. J.; Scholl, M.; Grubbs, R. H. J. Org. Chem. 1998, 63, 4291-4298. d) Weatherhead, G. S.; Ford, J. G.; Alexanian, E. J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 1828-1829. e) Choi, T.-L.; Grubbs, R. H. Chem. Commun. 2001, 2648-2649. f) Stapper, C.; Blechert, S. Eur. J. Org. Chem. 2002, 16, 2855-2858.
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    • For further examples of tandem ring rearrangement (RCM-ROM-RCM) metathesis reactions, see: a) Zuercher, W. J.; Hashimoto, M.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 6634-6640. b) Burke, S. D.; Quinn, K J.; Chen, V. J. J. Org. Chem. 1998, 63, 8626-8627. c) Zuercher, W. J.; Scholl, M.; Grubbs, R. H. J. Org. Chem. 1998, 63, 4291-4298. d) Weatherhead, G. S.; Ford, J. G.; Alexanian, E. J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 1828-1829. e) Choi, T.-L.; Grubbs, R. H. Chem. Commun. 2001, 2648-2649. f) Stapper, C.; Blechert, S. Eur. J. Org. Chem. 2002, 16, 2855-2858.
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    • For further examples of tandem ring rearrangement (RCM-ROM-RCM) metathesis reactions, see: a) Zuercher, W. J.; Hashimoto, M.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 6634-6640. b) Burke, S. D.; Quinn, K J.; Chen, V. J. J. Org. Chem. 1998, 63, 8626-8627. c) Zuercher, W. J.; Scholl, M.; Grubbs, R. H. J. Org. Chem. 1998, 63, 4291-4298. d) Weatherhead, G. S.; Ford, J. G.; Alexanian, E. J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 1828-1829. e) Choi, T.-L.; Grubbs, R. H. Chem. Commun. 2001, 2648-2649. f) Stapper, C.; Blechert, S. Eur. J. Org. Chem. 2002, 16, 2855-2858.
    • (1998) J. Org. Chem. , vol.63 , pp. 4291-4298
    • Zuercher, W.J.1    Scholl, M.2    Grubbs, R.H.3
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    • For further examples of tandem ring rearrangement (RCM-ROM-RCM) metathesis reactions, see: a) Zuercher, W. J.; Hashimoto, M.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 6634-6640. b) Burke, S. D.; Quinn, K J.; Chen, V. J. J. Org. Chem. 1998, 63, 8626-8627. c) Zuercher, W. J.; Scholl, M.; Grubbs, R. H. J. Org. Chem. 1998, 63, 4291-4298. d) Weatherhead, G. S.; Ford, J. G.; Alexanian, E. J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 1828-1829. e) Choi, T.-L.; Grubbs, R. H. Chem. Commun. 2001, 2648-2649. f) Stapper, C.; Blechert, S. Eur. J. Org. Chem. 2002, 16, 2855-2858.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 1828-1829
    • Weatherhead, G.S.1    Ford, J.G.2    Alexanian, E.J.3    Schrock, R.R.4    Hoveyda, A.H.5
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    • 0035930791 scopus 로고    scopus 로고
    • For further examples of tandem ring rearrangement (RCM-ROM-RCM) metathesis reactions, see: a) Zuercher, W. J.; Hashimoto, M.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 6634-6640. b) Burke, S. D.; Quinn, K J.; Chen, V. J. J. Org. Chem. 1998, 63, 8626-8627. c) Zuercher, W. J.; Scholl, M.; Grubbs, R. H. J. Org. Chem. 1998, 63, 4291-4298. d) Weatherhead, G. S.; Ford, J. G.; Alexanian, E. J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 1828-1829. e) Choi, T.-L.; Grubbs, R. H. Chem. Commun. 2001, 2648-2649. f) Stapper, C.; Blechert, S. Eur. J. Org. Chem. 2002, 16, 2855-2858.
    • (2001) Chem. Commun. , pp. 2648-2649
    • Choi, T.-L.1    Grubbs, R.H.2
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    • For further examples of tandem ring rearrangement (RCM-ROM-RCM) metathesis reactions, see: a) Zuercher, W. J.; Hashimoto, M.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 6634-6640. b) Burke, S. D.; Quinn, K J.; Chen, V. J. J. Org. Chem. 1998, 63, 8626-8627. c) Zuercher, W. J.; Scholl, M.; Grubbs, R. H. J. Org. Chem. 1998, 63, 4291-4298. d) Weatherhead, G. S.; Ford, J. G.; Alexanian, E. J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 1828-1829. e) Choi, T.-L.; Grubbs, R. H. Chem. Commun. 2001, 2648-2649. f) Stapper, C.; Blechert, S. Eur. J. Org. Chem. 2002, 16, 2855-2858.
    • (2002) Eur. J. Org. Chem. , vol.16 , pp. 2855-2858
    • Stapper, C.1    Blechert, S.2
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    • For further examples of [2,3]-Wittig-Still rearrangements, see: a) Ovaa, H.; Lastdrager, H. B.; Codee, J. D. C.; van der Marel, G. A.; Overkleeft, H. S.; van Boom, J. H. J. Chem. Soc., Perkin Trans. 1 2002, 21, 2370-2377. b) Riether, D.; Mulzer, J. Org. Lett. 2000, 2, 3139-3141.
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    • Riether, D.1    Mulzer, J.2
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    • note
    • As an analogue of 3, we synthesized Boc-piperidine and mixed it with 1 equiv of 3-phenylpropinoyl-piperidine. The mixture was dissolved in methylene chloride and treated with TFA. After 1 h the Boc-group was cleaved, while the triple bond had not reacted, as indicated by TLC and a NMR analysis of the crude mixture. After subsequent hydrogenation with Lindlar catalyst in methanol for 12 h at room temperature and conventional workup, the NMR spectra of the reaction residue showed the unchanged TFA salt of piperidine, together with stereoselective formation of the cis-cinammoyl protected piperidine in high yield.


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