Synthesis of (±)-Crotomachlin

Synlett

Volumn 1996, Issue 2, 1996, Pages 141-142

  Teramoto, Toshiyuki ^a   Yuno, Takeo ^a   Morita, Hajime ^a   Katsumura, Shigeo ^a,b   Sakaguchi, Kazuhiko ^a   Isoe, Sachihiko ^a  

^a Osaka Prefecture University   (Japan)

^b KWANSEI GAKUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011841503     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5358     Document Type: Article

References (22)

1. Personal communication from Prof. Isao Kubo at University of California, Berkeley, to whom we are very grateful.
2. (a) Herlem, D.; Khoung-Huu, F.; Kende, A. S. Tetrahedron Lett. 1993, 34, 5587.
3. (b) Herlem, D.; Kervagoret, J.; Yu, D.; Khoung-Huu, F.; Kende, A. S. Tetrahedron 1993, 49, 607.
4. (a) Forskolin and several of its analogs are known as activators of adenylate cyclase which have a number of physiological effects and considerable therapeutic potentials. Schreiber, S. L. C&E News 1992, Oct. 26, 22. Seamon, K. B. Ann. Rep. Med. Chem. 1984, 19, 293.
5. (a) Forskolin and several of its analogs are known as activators of adenylate cyclase which have a number of physiological effects and considerable therapeutic potentials. Schreiber, S. L. C&E News 1992, Oct. 26, 22. Seamon, K. B. Ann. Rep. Med. Chem. 1984, 19, 293.
6. (b) Identification: Bhat, S. V.; Bajwa, B. S.; Dornauer, H.; de Souza, N. J. Tetrahedron Lett. 1977, 19, 1669.
7. Synthesis of 2, unpublished result.
8. 3) δ 0.96 (s, 3 H), 1.08(s, 9 H), 1.22 (s, 3 H), 1.34 (s, 3 H), 1.40 (s, 3 H), 0.70 - 1.70 (m, 8 H), 2.90 (br d, 1H, J = 9.3 Hz), 3.12 (d, 1 H, J = 3.4 Hz), 3.46 (d, 1 H, J = 9.0 Hz), 3.96 (dd, 1H, J = 11.3, 3.7 Hz), 4.04 (s, 1 H), 4.13 (dd, 1 H, J = 11.3, 2.7 Hz), 4.28 (d, 1H, J = 2.4 Hz), 7.38 - 7.68 (m, 10 H). (Matrix Presented)
9. Katsumura, S.; Kimura, A.; Isoe, S. Tetrahedron 1989, 45, 1337.
10. (a) Yamada, S.; Takayama, H. J. Syn. Org. Chem. Jpn. 1988, 46, 893.
11. (b) Yamada, S.; Ohsawa, H.; Suzuki, T.; Takayama, H. J. Org. Chem. 1986, 51, 4934.
12. (c) Tao, Y. T.; Liu, C. L.; Lee, S. J. J. Org. Chem. 1986, 51, 4718.
13. (d) Chou, T. S.; Tso, H. H.; Chang, L. J. J. Chem. Soc., Chem. Commun. 1985, 236.
14. (e) Chou, T. S.; Tso, H. H.; Chang, L. J. J. Chem. Soc., Chem. Commun. 1984, 1323.
15. (f) Yamada, S.; Suzuki, T.; Takayama, H.; Miyamoto, K.; Matsunaga, I.; Nawata, Y. J. Org. Chem. 1983, 48, 3483.
16. (g) Yamada, S.; Ohsawa, H.; Suzuki, T.; Takayama, H. Chem. Lett. 1983, 1003.
17. 3) δ 200.8, 149.0, 141.7, 133.6, 133.5, 130.2, 110.2, 64.2, 56.9, 44.4, 41.0, 38.0, 32.9, 32.6, 22.4, 21.5, 18.5, 13.8, 11.7.
18. Dauben, W. G.; Michno, D. M. J. Org. Chem. 1977, 42, 682.
19. (a) Sharpless, K. B.; Michaelson, R. C. J. Am. Chem. Soc. 1973, 95, 6136.
20. (b) Itoh, T.; Jitsukawa, K.; Kaneda, K.; Teranishi, S. J. Am. Chem. Soc. 1979, 101, 159.
21. 3) δ 141.5, 134.5, 133.2, 110.6, 65.5, 64.5, 64.2, 54.8, 53.9, 44.4, 43.4, 36.8, 34.3, 33.2, 26.2, 24.5, 22.9, 18.8, 18.5, 12.0.
22. -1.