A facile construction of the quadranoid skeleton: Application to the total synthesis of (±)-suberosenone

Organic Letters

Volumn 2, Issue 13, 2000, Pages 1951-1953

  Lee, Hee Yoon ^a   Kim, Byung Gyu ^a  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000313688     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0060230     Document Type: Article

References (23)

1. Bokesch, H. R.; McKee, T. C.; Cardellina II, J. H.; Boyd, M. R. Tetrahedron Lett. 1996, 37, 3259.
2. Calton, G. J.; Ranier, R. L.; Espenshade, M. A. J. Antibiot. 1973, 31, 38.
3. Bokesch, H. R.; Blunt, J. W.; Westergaard, C. K.; Cardellina, J. H., II; Johnson, T. R.; Michael, J. A.; McKee, T. C.; Hollingshead, M. G.; Boyd, M. R. J. Nat. Prod. 1999, 62, 633.
4. Ermolenko, M. S.; Pipelier, M. Tetrahedron Lett. 1997, 38, 5975.
5. Smith, A. B., III; Konopelski, J. P.; Wexler, B. A.; Prengler, P. A. J. Am. Chm. Soc. 1991, 113, 3533.
6. Gordeeva, E. V.; Lushnikov, D. E.; Zefirov, N. S. Tetrahedron 1992, 48, 3787.
7. Lee, H. Y.; Kim, B. G. Book of Abstracts, 11lth ICOS, Amsterdam, The Netherlands; IUPAC & KNCV: Amsterdam, 1996; PO-026.
8. Clive, D. L. J.; Magnuson, S. R.; Manning, H. W.; Mayhew, D. L. J. Org. Chem. 1996, 61, 2095.
9. Froborg, J.; Magnusson, G. J. Am. Chem. Soc. 1978, 100, 6728.
10. Miwa, K.; Aoyama, T.; Shioiri, T. Synlett 1994, 107.
11. Clive, D. L. J.; Beaulieu, P. L.; Set, L. J. Org. Chem. 1984, 49, 1313.
12. Mancuso, A. J.; Huang, S.-L.; Swern, D. J. Org. Chem. 1978, 43, 2480.
13. Stork, G.; Mook, R., Jr. J. Am. Chem. Soc. 1987, 109, 2829.
14. MM2 minimized energy for the conformation of 6 to form the intermediate for the observed product was 1.4 kcal/mol lower than that for the other product.
15. The chemoselectivity was presumed to result from the steric bias imposed by the gem-dimethyl group since the selectivity reversed when the desdimethyl analogue of 7 was subjected to the ozonolysis conditions.
16. Molander, G. A.; Hahn, G. J. Org. Chem. 1986, 51, 1135.
17. Reich, H. J.; Reich, I. L.; Renga, J. M. J. Am. Chem. Soc. 1973, 95, 5813.
18. Gribble, G. W.; Nutaitis, C. F. Org. Prep. Proc. Int. 1985, 17, 317.
19. Grieco, P. A.; Gilman, S.; Nishizawa, M. J. Org. Chem. 1976, 41, 1485.
20. Wender, P. A.; Wolanin, D. J. J. Org. Chem. 1985, 50, 4418.
21. Barton, D. H. R.; McCombie, S. W. J. Chem. Soc., Perkin Trans. 1 1975, 1574.
22. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639.
23. 1H NMR spectrum of natural suberosenone was superimposable to that of synthetic suberosenone.