A concise, enantioselective synthesis of (-)- and (+)-hongconin

Journal of Organic Chemistry

Volumn 61, Issue 2, 1996, Pages 455-458

  Deshpande, Prashant P ^a   Price, Kenneth N ^a   Baker, David C ^a  

^a UNIVERSITY OF TENNESSEE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; HONGCONIN; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER;

EID: 0030023639     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951602h     Document Type: Article

References (33)

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19. (b) Kraus and co-workers had previously developed the use of 6 in phthalide annulation chemistry to synthesize racemic kalafungin, pachybasin, and chrysophanol: Kraus, G. A.; Cho, H.; Crowley, S.; Roth, B.; Sugimoto, H.; Prugh, S. J. Org. Chem. 1983, 48, 3439.
20. (c) For Swenton and co-workers' synthesis of hongconin, see: Swenton, J. S.; Frekos, J. N.; Dalidowicz, P.; Kerns, M. L. J. Org. Chem. 1996, 61, 459-464.
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23. This achievement is shared with J. S. Swenton and co-workers, whose work is described in the accompanying paper.
24. Such a rationale was most probably responsible for the uniform adoption in the literature of structure 1 to represent hongconin, even though its absolute configuration had not been experimentally established.
25. For example, nanaomycin D and kalafungin are enantiomers, and the antibiotics granaticin and medermycin have been found in either enantiomeric form. See ref 9.
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27. 3) δ 1.39 (d, 3H, J = 6.80 Hz), 1.62 (d, 3H, J = 6.60 Hz), 3.95 (s, 3H), 4.23 (q, 1H, J = 6.85 Hz), 4.94 (q, 1H, J = 6.64 Hz), 7.54 (dd, 1H, J = 0.88 Hz, J = 7.67 Hz), 7.68-7.76 (m, 2H); MS (m/z) 285, 203. Some epimerization was noted, presumably at C-I, as had previously been reported for the structurally similar 2 and 3 (ref 3e). C-1 epimerizations in such systems have been exploited by Tatsuta and co-workers as a means of obtaining the desired stereochemistry at that position during a synthesis of kalafungin (ref 9).
28. 13C NMR, IR, and mass spectral data (see Experimental Section).
29. f = 0.45).
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