Total synthesis of the structure proposed for prekinamycin

Journal of Organic Chemistry

Volumn 61, Issue 17, 1996, Pages 5722-

  Hauser, Frank M ^a   Zhou, Maotang ^a  

^a STATE UNIVERSITY OF NEW YORK   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; PREKINAMYCIN; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; NUCLEAR MAGNETIC RESONANCE; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 16044372677     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9609891     Document Type: Article

References (17)

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4. Hauser, F. M.; Rhee, R. P. J Org. Chem. 1978, 43, 178. For use of this reaction in natural products syntheses, see: Hauser, F. M.; Mal, D. J. Am. Chem. Soc. 1984, 706, 1098. Hauser, F. M.; Prasanna, S. Tetrahedron 1984, 40, 4711. Hauser, F. M.; Chakrapani, S.; Ellenberger, W. P. J. Org. Chem. 1991, 56, 5248. Hauser, F. M.; Tommassi, R. A. J. Org. Chem, 1991, 56, 5758.
5. Hauser, F. M.; Rhee, R. P. J Org. Chem. 1978, 43, 178. For use of this reaction in natural products syntheses, see: Hauser, F. M.; Mal, D. J. Am. Chem. Soc. 1984, 706, 1098. Hauser, F. M.; Prasanna, S. Tetrahedron 1984, 40, 4711. Hauser, F. M.; Chakrapani, S.; Ellenberger, W. P. J. Org. Chem. 1991, 56, 5248. Hauser, F. M.; Tommassi, R. A. J. Org. Chem, 1991, 56, 5758.
6. Hauser, F. M.; Rhee, R. P. J Org. Chem. 1978, 43, 178. For use of this reaction in natural products syntheses, see: Hauser, F. M.; Mal, D. J. Am. Chem. Soc. 1984, 706, 1098. Hauser, F. M.; Prasanna, S. Tetrahedron 1984, 40, 4711. Hauser, F. M.; Chakrapani, S.; Ellenberger, W. P. J. Org. Chem. 1991, 56, 5248. Hauser, F. M.; Tommassi, R. A. J. Org. Chem, 1991, 56, 5758.
7. Hauser, F. M.; Rhee, R. P. J Org. Chem. 1978, 43, 178. For use of this reaction in natural products syntheses, see: Hauser, F. M.; Mal, D. J. Am. Chem. Soc. 1984, 706, 1098. Hauser, F. M.; Prasanna, S. Tetrahedron 1984, 40, 4711. Hauser, F. M.; Chakrapani, S.; Ellenberger, W. P. J. Org. Chem. 1991, 56, 5248. Hauser, F. M.; Tommassi, R. A. J. Org. Chem, 1991, 56, 5758.
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9. While this work was in progress, condensation of an indenone with a (phenylsulfonyl)isobenzofuranone was reported. Mal, D.; Hazra, N. K. Tetrahedron Lett. 1986, 37, 2641.
10. For the rearrangement of dihydrocoumarins to indanones, see: Loudon, J. D.; Razdan, R. K. J. Chem. Soc. 1954, 4299.
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13. This widely used procedure developed by Saegusa et al. for the preparation of α,β-unsaturated enones has not previously been used to prepare indenones from indanones. Ito, Y.; Hirao, T.; Saegusa, T. J. Org. Chem. 1978, 43, 1011.
14. Balogh, V.; Fetizon, M.; Golfier, M. J. Org. Chem. 1971, 36, 1339.
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16. 11
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