Total synthesis of dysidiolide

Journal of the American Chemical Society

Volumn 119, Issue 51, 1997, Pages 12425-12431

  Corey, E J ^a   Roberts, Bryan E ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHOPROTEIN PHOSPHATASE INHIBITOR;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER; DRUG ISOLATION; DRUG SYNTHESIS; SPONGE (PORIFERA); STEREOCHEMISTRY;

EID: 0031585678     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja973023v     Document Type: Article

References (34)

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8. Slow addition of the α,β-enone to the TMSLi was necessary in order to minimize the formation of dimeric side products.
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10. 9b (2.6:1).
11. 9b (2.6:1).
12. 9b (2.6:1).
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15. The crude reaction mixture also contained the 65 diastereomer of 6 (21%), which was removed during silica gel radial chromatography.
16. Efforts to improve the diastereoselectivity of the hydrogenation were unproductive. It appears that the cyclohexyl ring containing the exocyclic olefin is distorted out of the usual chair conformation as a result of steric interactions between the 1,3-diaxial methyl groups. As a result, the two faces of the olefin are nearly equally accessible to hydrogenation.
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18. Approximately 7% of a minor (nonrearranged) product derived from elimination of the initially formed carbocation of 7 was isolated from this reaction. After TBS ether cleavage, this product was separated from 8 by silica gel radial chromatography.
19. We are indebted to Dr. Marcus Semones for carrying out the X-ray crystallographic analysis. Detailed X-ray crystallographic data are available from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.
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28. For other examples of diastereoselective CBS reductions, see (a) Corey, E. J.; Helal, C. J. Tetrahedron Lett., in press (Cicaprost ω-side chain); (b) Rao, M. N.; McGuigan, M. A.; Zhang, X.; Shaked, Z.; Kinney, W. A.; Bulliard, M.; Laboue, B.; Lee, N. E. J. Org. Chem. 1997, 62, 4541 (steroidal side chains); (c) Tschaen, D. M.; Abramson, L.; Cai, D.; Desmond, R.; Dolling, U.-H.; Frey, L.; Karady, S.; Shi, Y.-J.; Verhoeven, T. R. J. Org. Chem. 1995, 60, 4324 (MK-0499).
29. For other examples of diastereoselective CBS reductions, see (a) Corey, E. J.; Helal, C. J. Tetrahedron Lett., in press (Cicaprost ω-side chain); (b) Rao, M. N.; McGuigan, M. A.; Zhang, X.; Shaked, Z.; Kinney, W. A.; Bulliard, M.; Laboue, B.; Lee, N. E. J. Org. Chem. 1997, 62, 4541 (steroidal side chains); (c) Tschaen, D. M.; Abramson, L.; Cai, D.; Desmond, R.; Dolling, U.-H.; Frey, L.; Karady, S.; Shi, Y.-J.; Verhoeven, T. R. J. Org. Chem. 1995, 60, 4324 (MK-0499).
30. For other examples of diastereoselective CBS reductions, see (a) Corey, E. J.; Helal, C. J. Tetrahedron Lett., in press (Cicaprost ω-side chain); (b) Rao, M. N.; McGuigan, M. A.; Zhang, X.; Shaked, Z.; Kinney, W. A.; Bulliard, M.; Laboue, B.; Lee, N. E. J. Org. Chem. 1997, 62, 4541 (steroidal side chains); (c) Tschaen, D. M.; Abramson, L.; Cai, D.; Desmond, R.; Dolling, U.-H.; Frey, L.; Karady, S.; Shi, Y.-J.; Verhoeven, T. R. J. Org. Chem. 1995, 60, 4324 (MK-0499).
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32. 1
33. Obtained from Dr. Sarath P. Gunasekera, Harbor Branch Oceanographic Institute, Fort Pierce, FL.
34. This research was assisted financially by a grant from the National Institutes of Health.