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Volumn 62, Issue 21, 1997, Pages 7508-7577

Preparation of a C-1 oxygenated taxane a ring via a highly efficient diels-alder strategy utilizing an α-(aroyloxy) enone captodative dienophile

Author keywords

[No Author keywords available]

Indexed keywords

CONTROL EXPERIMENTS; DIELS-ALDER STRATEGY; HETERO-DIELS-ALDER; IMPURITIES IN; ION TRANSFER; REACTION SOLVENTS; SIDE REACTIONS; THERMAL ELIMINATIONS;

EID: 0000793593     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo9711753     Document Type: Article
Times cited : (9)

References (47)
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    • For reviews dealing with the construction of the taxane A ring, see refs 1b,c,d. For other recent synthetic approaches to the taxane A ring, see
    • For reviews dealing with the construction of the taxane A ring, see refs 1b,c,d. For other recent synthetic approaches to the taxane A ring, see: (a) Alcaraz, L.; Harnett, J. J.; Mioskowski, C.; LeGall, T.; Shin, D.-S.; Falck, J. R. J. Org. Chem. 1995, 60, 7209.
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    • For Diels-Alder approaches to the taxane A ring using captodative dienophiles but where the C-1 oxygen is not directly established in the cycloaddition step, see
    • For Diels-Alder approaches to the taxane A ring using captodative dienophiles but where the C-1 oxygen is not directly established in the cycloaddition step, see: (a) Masamune, T.; Fukuzawa, A.; Furusaki, A.; Ikura, M.; Matsue, H.; Kaneko, T.; Abiko, A.; Sakamoto, N.; Tanimoto, N.; Murai, A. Bull. Chem. Soc. Jpn. 1987, 60, 1001.
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    • After completion of most of the work described herein, Funk and Yost reported a related approach to that outlined in this paper; however they employed a 2-(acyloxy)acrolein rather than an α-(aroyloxy) enone as the captodative dienophile
    • After completion of most of the work described herein, Funk and Yost reported a related approach to that outlined in this paper; however they employed a 2-(acyloxy)acrolein rather than an α-(aroyloxy) enone as the captodative dienophile: Funk, R. L.; Yost, K. J., III. J. Org. Chem. 1996, 61, 2598.
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    • note
    • The dienophile was precomplexed with the Lewis acid, and the following addition adducts were obtained in a 2:1 ratio: (Chemical Equation Presented)


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