A short enantioselective total synthesis of dammarenediol II

Journal of the American Chemical Society

Volumn 118, Issue 36, 1996, Pages 8765-8766

  Corey, E J ^a   Lin, Shouzhong ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DAMMARENEDIOL II; SQUALENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG ANALYSIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0029793921     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9620806     Document Type: Article

References (31)

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24. For background, see: (a) Taylor, S. K. Org. Prep. Proced. Intl. 1992, 24, 245. (b) Johnson, W. S. Tetrahedron 1991, 47 (41), xi. (c) Corey, E. J.; Lee, J.; Liu, D. R. Tetrahedron Lett. 1994, 35, 9149. (d) Corey, E. J.; Lee. J. J. Am. Chem. Soc. 1993, 115, 8873. (e) Johnson, W. S.; Plummer, M. S.; Reddy, S. P.; Bartlett, W. R. J. Am. Chem. Soc. 1993, 115, 515. (f) Tanis, S. P.; Chuang, Y.-H.; Head, D. B. J. Org. Chem. 1988, 53, 4929.
25. For background, see: (a) Taylor, S. K. Org. Prep. Proced. Intl. 1992, 24, 245. (b) Johnson, W. S. Tetrahedron 1991, 47 (41), xi. (c) Corey, E. J.; Lee, J.; Liu, D. R. Tetrahedron Lett. 1994, 35, 9149. (d) Corey, E. J.; Lee. J. J. Am. Chem. Soc. 1993, 115, 8873. (e) Johnson, W. S.; Plummer, M. S.; Reddy, S. P.; Bartlett, W. R. J. Am. Chem. Soc. 1993, 115, 515. (f) Tanis, S. P.; Chuang, Y.-H.; Head, D. B. J. Org. Chem. 1988, 53, 4929.
26. For background, see: (a) Taylor, S. K. Org. Prep. Proced. Intl. 1992, 24, 245. (b) Johnson, W. S. Tetrahedron 1991, 47 (41), xi. (c) Corey, E. J.; Lee, J.; Liu, D. R. Tetrahedron Lett. 1994, 35, 9149. (d) Corey, E. J.; Lee. J. J. Am. Chem. Soc. 1993, 115, 8873. (e) Johnson, W. S.; Plummer, M. S.; Reddy, S. P.; Bartlett, W. R. J. Am. Chem. Soc. 1993, 115, 515. (f) Tanis, S. P.; Chuang, Y.-H.; Head, D. B. J. Org. Chem. 1988, 53, 4929.
27. For background, see: (a) Taylor, S. K. Org. Prep. Proced. Intl. 1992, 24, 245. (b) Johnson, W. S. Tetrahedron 1991, 47 (41), xi. (c) Corey, E. J.; Lee, J.; Liu, D. R. Tetrahedron Lett. 1994, 35, 9149. (d) Corey, E. J.; Lee. J. J. Am. Chem. Soc. 1993, 115, 8873. (e) Johnson, W. S.; Plummer, M. S.; Reddy, S. P.; Bartlett, W. R. J. Am. Chem. Soc. 1993, 115, 515. (f) Tanis, S. P.; Chuang, Y.-H.; Head, D. B. J. Org. Chem. 1988, 53, 4929.
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29. To the best of our knowledge, this approach has not previously been demonstrated despite the vast amount of effort which has been directed at the synthesis of steroid-like ring systems.
30. The phenylcarbamate moiety survived the vigorous acid treatment required for the acid-catalyzed aldol conversion to 10 in contrast to other derivatives such as silyl ethers or carboxylic esters.
31. Dammarenediol I was obtained from the later Chromatographic fractions.