Total synthesis of the cytotoxic annonaceous acetogenin (30S)-bullanin

Tetrahedron Letters

Volumn 39, Issue 11, 1998, Pages 1303-1306

  Marshall, James A ^a   Hinkle, Kevin W ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOGENIN; BULLANIN; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS;

EID: 0032510370     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10739-0     Document Type: Article

References (22)

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2. 2. Cf. Zeng, L.; Ye, Q.; Oberlies, N. H.; Shi, G.; Gu, Z.-M.; He, K., McLaughlin, J. L. Nat. Prod. Reports 1996, 275.
3. 3. Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1997, 62, 5989.
4. 4. Marshall, J. A.; Chen, M. J. Org. Chem. 1997, 62, 5996.
5. 5. For recent reviews of other synthetic approaches, see Figadere, B. Accts. Chem. Res. 1995, 28, 359. Marshall, J. A.; Hinkle, K. W.; Hagedorn, C. E. Israel J. Chem. 1997, 37, 97. See also Hoye, T. R.; Ye, Z. J. Am. Chem. Soc. 1996, 37, 7001.
6. 5. For recent reviews of other synthetic approaches, see Figadere, B. Accts. Chem. Res. 1995, 28, 359. Marshall, J. A.; Hinkle, K. W.; Hagedorn, C. E. Israel J. Chem. 1997, 37, 97. See also Hoye, T. R.; Ye, Z. J. Am. Chem. Soc. 1996, 37, 7001.
7. 5. For recent reviews of other synthetic approaches, see Figadere, B. Accts. Chem. Res. 1995, 28, 359. Marshall, J. A.; Hinkle, K. W.; Hagedorn, C. E. Israel J. Chem. 1997, 37, 97. See also Hoye, T. R.; Ye, Z. J. Am. Chem. Soc. 1996, 37, 7001.
8. 6. These materials occur as nearly inseparable mixtures which are purified following mutiple solvent partitionings, multiple column chromatography, HPLC, and radial chromatography. It is not uncommon to obtain only 5-10 mg of pure material from 15 kg of dried stem bark. Cf. Zhao, G.; Chao, J.-F.; Zeng, L.; Rieser, M. J.; McLauglin, J. L. Bioorg. Med. Chem. 1996, 4, 25.
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19. 15. Previous work revealed a significant decrease in diastereoselectivity for additions of long-chain oxygenated stannanes compared to the crotyl analogues. This was not observed in the case of the long-chain stannane 17 and aldehyde 10. Marshall, J. A.; Welmaker, G. S. J. Org. Chem. 1994, 59, 4122.
20. 16. Cf. Sonogashira, in Comprehensive Organic Synthesis. Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 3. Chapter 2.4.
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