A facile entry into naphthopyran quinones via an annelation reaction of levoglucosenone. The total synthesis of (-)-hongconin

Journal of Organic Chemistry

Volumn 61, Issue 2, 1996, Pages 459-464

  Swenton, John S ^a   Freskos, John N ^a   Dalidowicz, Peter ^a   Kerns, Michael L ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

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

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030032644     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951607e     Document Type: Article

References (40)

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15. Structure of hongconin: Zhengxiong, C.; Huizhu, H.; Chengrui, W.; Yuhui, L.; Jianmi, D.; Sankawa, U.; Noguchi, H.; Iitaka, Y. Heterocycles 1984, 22, 691; Chem. Pharm. Bull. 1986, 14, 2743.
16. Structure of hongconin: Zhengxiong, C.; Huizhu, H.; Chengrui, W.; Yuhui, L.; Jianmi, D.; Sankawa, U.; Noguchi, H.; Iitaka, Y. Heterocycles 1984, 22, 691; Chem. Pharm. Bull. 1986, 14, 2743.
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22. 9b have also prepared (- )-hongconin, and this is being published in the accompanying article: Deshpande, P. P.; Price, K. N.; Baker, D. C. J. Org. Chem. 1996, 61, 455-458. We thank these authors for agreeing to joint publication of these results
23. Swenton, J. S.; Freskos, J. N.; Morrow, G. W.; Sercel, A. D. Tetrahedron 1984, 40, 4625. Morrow, G. W.; Swenton, J. S.; Filppi, Joyce, A.; Wolgemuth, R. L. J. Org. Chem., 1987, 52, 713 and references cited therein.
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25. For a general route to cyanophthalides (3-cyano-1(3H)-isobenzo-furanones), see: Freskos, J. N.; Morrow, G. W.; Swenton, J. S. J. Org. Chem. 1985, 50, 805.
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29. 1H NMR spectrum was also similar to the spectrum of the "cis-isomer of (+)-hongconin", (1S,3R)-9-methoxy-1,3-dimethyl-1H-naphtho[2,3-c;]pyran-4,5,10(3H)-trione, supplied by Professor David Baker.
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31. We thank Professor V. Rawal for suggesting we reexamine this reaction.
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34. The material used in this work was prepared in an advanced organic laboratory class, and the Experimental Section was adapted from a report of Mr. Michael Capperelli. We thank the class for preparing over 100 g of material and Mr. Capperelli for the use of his report.
35. Blankenship, R. M.; Burdett, K. A.; Swenton, J. S. J. Org. Chem. 1974, 39, 2300.
36. Note that this material is extensively racemized from the zinc/ copper reduction step so the rotation value is low.
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39. 1H NMR spectrum in benzene for the benefit of future investigators.
40. 1H NMR spectrum of late fractions from the column. This material was not present in starting 17 so in these runs a small amount of isomerization aceompanies this step.