Enantioselective total syntheses of kudtriol, 5-epi-kudtriol and their C-11 epimers

Tetrahedron Asymmetry

Volumn 11, Issue 8, 2000, Pages 1819-1826

  Zhou, Gang ^a   Gao, Xiaolei ^a   Zhang, Zhe ^a   Li, Weidong Z ^a   Li, Yulin ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

SESQUITERPENE DERIVATIVE;

ARTICLE; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; HYDROXYLATION; NONHUMAN; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034608080     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00119-1     Document Type: Article

References (18)

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3. Teresa, J. P.; Barrero, A. F.; Feliciano, A. S.; Medarde, M. Tetrahedron Lett. 1978, 43, 4141.
4. Teresa, J. P.; Barrero, A. F.; Feliciano, A. S.; Medarde, M. Phytochemistry 1980, 19, 2155.
5. Harapanhalli, R. S. J. Chem. Soc., Perkin Trans. 1 1988, 3149.
6. Prepared from (+)-carvone by Zn-NaOH reduction.
7. Xiong, Z. M.; Yang, J.; Li, Y. L. Tetrahedron: Asymmetry 1996, 7, 2607.
8. For a review on the deoxygenation of carbonyl compounds; see: Yamamura, S.; Nishiyama, S. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 8, p. 307.
9. For a review on epoxidation of alkenes, see: Rao, A. S. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 7, p. 357.
10. Kolb, H. C.; Vannieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
11. Takahata, H.; Kouno, S.; Momose, T. Tetrahedron: Asymmetry 1995, 6, 1085.
12. Wang, Z.-M.; Shen, M. Tetrahedron: Asymmetry 1997, 8, 3393.
13. White, J. D.; Shin, H.; Khim, T. S.; Cutshall, N. S. J. Am. Chem. Soc. 1997, 119, 240.
14. Takatsuto, S.; Yazawa, N.; Ishiguro, M.; Morisaki, M.; Ikekawa, M. J. Chem. Soc., Perkin Trans. 1 1984, 139.
15. Jakupovic, J.; Lehmann, L.; Bohlmann, F.; King, R. M.; Robinson, H. Phytochemistry 1988, 27, 3831.
16. 2PHAL are mismatching ligands in this AD reaction. See also: Chen, Y. G.; Xiong, Z. M.; Gang, Z.; Liu, L.; Li, Y. L. Tetrahedron: Asymmetry 1998, 9, 1923.
17. 6 as cooxidant gave the corresponding triol mixture 2a and 2b (3a and 3b) in a ratio of ca. 1:1.
18. Authentic samples of natural kudtriol and 5-epi-kudtriol are not available for direct comparison.