Enantioselective synthesis of N1999A2

Journal of the American Chemical Society

Volumn 128, Issue 46, 2006, Pages 14825-14827

  Ji, Nan ^a   O'Dowd, Hardwin ^a   Rosen, Brad M ^a   Myers, Andrew G ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

N 1999A2; UNCLASSIFIED DRUG; ZINOSTATIN DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; STRUCTURE ANALYSIS;

ENEDIYNES; EPOXY COMPOUNDS; HUMANS; NAPHTHALENES; STEREOISOMERISM;

EID: 33845214779     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0662467     Document Type: Article

References (28)

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17. (S)-Glyceraldehyde acetonide (12) was synthesized in one step from (R)-(-)-2,2-dimethyl-1,3-dioxolane-4-methanol (Alfa Aesar) by the method of Janson et al. See: Janson, M.; Kvarnström, I.; Svensson, S. C. T.; Samuelsson, B. C. B. Synthesis 1993, 129.
18. Myers, A. G.; Hammond, M.; Wu, Y.; Xiang, J.-N.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1996, 118, 10006.
19. In the absence of any lithium halide additive, Wittig coupling of 13 and 14 using n-butyllithium as base afforded a 1.5:1 mixture of Z- and E-olefins, respectively. The undesired E-isomer could be transformed into a 55:45 mixture of E- and Z-isomers, respectively, by UV irradiation. See Supporting Information for details.
20. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
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22. In this application, acetonitrile was found to be a more effective solvent than dichloromethane, the solvent used by Sen et al. See: Sen, S. E.; Roach, S. L.; Boggs, J. K.; Ewing, G. H.; Magrath, J. J. Org. Chem. 1997, 62, 6684.
23. 1c
24. Mesitaldehyde dimethyl acetal (19) was synthesized in one step from mesitaldehyde as follows: camphorsulfonic acid (10 mg) was added to a solution of mesitaldehyde (3.00 g, 20.2 mmol, 1 equiv) and trimethyl orthoformate (3.22 g, 30.4 mmol, 1.5 equiv) in methanol (30 mL) at 23°C. After stirring at 23°C for 12 h, the reaction mixture was partitioned between ether (30 mL) and saturated aqueous sodium bicarbonate solution (30 mL). The aqueous layer was separated and further extracted with ether (30 mL). The organic extracts were combined, and the combined solution was dried over anhydrous sodium sulfate. The dried solution was filtered, and the filtrate was concentrated to provide mesitaldehyde dimethyl acetal (19) as a colorless oil (3.90 g, 99%).
25. Eglinton, G.; Galbreath, A. R. J. Chem. Soc. 1959, 889.
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27. (b) Myers, A. G.; Hogan, P. C.; Hurd, A. R.; Goldberg, S. D. Angew. Chem., Int. Ed. 2002, 41, 1062.
28. The diethylisopropylsilyl-protected naphthoic acid 4 was synthesized in two steps from the corresponding triisopropylsilyl-protected naphthoic acid; see Supporting Information. For synthesis of the triisopropylsilyl-protected naphthoic acid, see: Ji, N.; Rosen, B. M.; Myers, A. G. Org. Lett. 2004, 6, 4551.