What is the structure of glabrescol? Stereoselective synthesis reported glabrescol

Angewandte Chemie - International Edition

Volumn 39, Issue 14, 2000, Pages 2552-2554

  Hioki, Hideaki ^a   Kanehara, Chie ^a   Ohnishi, Yumiko ^a   Umemori, Yukiko ^a   Sakai, Hitoshi ^a   Yoshio, Suzuyo ^a   Matsushita, Masayuki ^a   Kodama, Mitsuaki ^a  

^a TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

Asymmetric synthesis; Natural products; Polyethers; Structure elucidation; Terpenoids

Indexed keywords

GLABRESCOL; TRITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; JAPAN; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034679506     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20000717)39:14<2552::AID-ANIE2552>3.0.CO;2-D     Document Type: Article

References (19)

1. W. W. Harding, P. A. Lewis, H. Jacobs, S. McLean, W. F. Reynolds, L.-L. Tay, J.-P. Yang, Tetrahedron Lett. 1995, 36, 9137.
2. For the synthetic studies of glabrescol, see: Y. Morimoto, T. Iwai, T. Yoshimura, T. Kinoshita, Bioorg. Med. Chem. Lett. 1998, 8, 2005.
3. For the stereoselective synthesis of trans-threo-penta (tetrahydrofuran), see: a) U. Koert, M. Stein, K. Harms, Angew. Chem. 1994, 106, 1238; Angew. Chem. Int. Ed. Engl. 1994, 33, 1180; b) U. Koert, M. Stein, H. Wagner, Chem. Eur. J. 1997, 3, 1170.
4. For the stereoselective synthesis of trans-threo-penta (tetrahydrofuran), see: a) U. Koert, M. Stein, K. Harms, Angew. Chem. 1994, 106, 1238; Angew. Chem. Int. Ed. Engl. 1994, 33, 1180; b) U. Koert, M. Stein, H. Wagner, Chem. Eur. J. 1997, 3, 1170.
5. For the stereoselective synthesis of trans-threo-penta (tetrahydrofuran), see: a) U. Koert, M. Stein, K. Harms, Angew. Chem. 1994, 106, 1238; Angew. Chem. Int. Ed. Engl. 1994, 33, 1180; b) U. Koert, M. Stein, H. Wagner, Chem. Eur. J. 1997, 3, 1170.
6. For our examples of natural product synthesis using baker's yeast reduction, see: a) M. Kodama, S. Yoshio, T. Tabata, Y. Deguchi, Y. Sekiya, Y. Fukuyama, Tetrahedron Lett. 1997, 38, 4627; b) H. Hioki, H. Ooi, Y. Mimura, S. Yoshio, M. Kodama, Synlett 1998, 729.
7. For our examples of natural product synthesis using baker's yeast reduction, see: a) M. Kodama, S. Yoshio, T. Tabata, Y. Deguchi, Y. Sekiya, Y. Fukuyama, Tetrahedron Lett. 1997, 38, 4627; b) H. Hioki, H. Ooi, Y. Mimura, S. Yoshio, M. Kodama, Synlett 1998, 729.
8. M. Kodama, H. Minami, Y. Mima, Y. Fukuyama, Tetrahedron Lett. 1990, 31, 4025. The optical purity was determined to be 98% ee by liquid chromatographic analysis using a chiral column.
9. The stereochemistry of 4 and 5 was determined by a modified Mosher's method. See Ref. [4a].
10. Z.-X. Wang, Y. Tu, M. Frohn, J.-R. Zhang, Y. Shi, J. Am. Chem. Soc. 1997, 119, 11224.
11. The stereochemistry of the Sharpless asymmetric epoxidation has been unambiguously established. See: a) M. G. Finn, K. B. Sharpless, Asymmetric Synthesis (Ed.: J. D. Morrison), Academic Press, New York, 1985, Chap. 8, p. 247; b) T. Katsuki, V. S. Martin, Org. React. 1996, 48, 1.
12. The stereochemistry of the Sharpless asymmetric epoxidation has been unambiguously established. See: a) M. G. Finn, K. B. Sharpless, Asymmetric Synthesis (Ed.: J. D. Morrison), Academic Press, New York, 1985, Chap. 8, p. 247; b) T. Katsuki, V. S. Martin, Org. React. 1996, 48, 1.
13. 1H NMR: δ = 0.07 (3H, s), 0.08 (3H, s), 0.85 (9H, s), 1.16 (3H, s), 1.18 (3H, s), 1.18 (3H, s), 1.19 (3H, s), 1.53-1.66 (2H, m), 1.79-1.97 (6H, m), 2.69-2.74 (2H, m), 3.03 (1H, dd, J = 3.9, 3.0 Hz), 3.71 (1H, dd, J = 7.2, 7.2 Hz), 3.92 (1H, dd, J = 7.0, 7.0 Hz).
14. I. Nagawa, T. Hata, Tetrahedron Lett. 1975, 1409.
15. 1H NMR: δ = 0.08 (6H, s), 0.86 (9H, s), 1.12 (3H, s), 1.14 (3H, s), 1.22(3H, s), 1.57 (3H, br.s), 1.20-2.40 (8H, m), 3.21 (1H dd, J = 8.8, 2.5 Hz), 3.54 (2H, d. J = 7.4 Hz), 3.74 (1H, t, J = 7.0 Hz), 3.80 (3H, s), 4.47 (1H, d, J = 11.0 Hz), 4.59 (1H, d, J = 11.0 Hz), 5.31 (1H, br.t, J = 7.7 Hz), 6.86 (2H, d, J = 8.8 Hz), 7.16-7.36 (7H, m).
16. The stereochemistry of diol 14 was based on the empirical rule. See: a) K. B. Sharpless, W. Amberg, Y. L. Bennani, G. A. Crispino, J. Hartung, K.-S. Jeong, H.-L. Kwong, K. Morikawa, Z.-M. Wang, D. Xu, X.-L. Zhang, J. Org. Chem. 1992, 57, 2768; b) H. Becker, S. B. King, M. Taniguchi, K. P. M. Vanhessche, K. B. Sharpless, J. Org. Chem. 1995, 60, 3940.
17. The stereochemistry of diol 14 was based on the empirical rule. See: a) K. B. Sharpless, W. Amberg, Y. L. Bennani, G. A. Crispino, J. Hartung, K.-S. Jeong, H.-L. Kwong, K. Morikawa, Z.-M. Wang, D. Xu, X.-L. Zhang, J. Org. Chem. 1992, 57, 2768; b) H. Becker, S. B. King, M. Taniguchi, K. P. M. Vanhessche, K. B. Sharpless, J. Org. Chem. 1995, 60, 3940.
18. The AD-mix-α oxidation afforded 14 and its diastereomer in the ratio of 5.2:1.
19. 13C NMR spectra of 1 when they were recorded at the lower concentration.