Total synthesis and absolute stereochemistry of plakortone E

Tetrahedron Letters

Volumn 47, Issue 14, 2006, Pages 2287-2290

  Akiyama, Megumi ^a   Isoda, Yuichi ^a   Nishimoto, Masato ^a   Narazaki, Maiko ^a   Oka, Hiroaki ^a   Kuboki, Atsuhito ^a   Ohira, Susumu ^a  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Absolute stereochemistry; Alkylidenecarbene; C H insertion; Plakortone E

Indexed keywords

EID: 33644747422     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.02.025     Document Type: Article

References (25)

1. A.D. Patil, A.J. Freyer, M.F. Bean, B.K. Carte, J.W. Westley, R.K. Johnson, and P. Lahouratate Tetrahedron 52 1996 377 394
2. F. Cafieri, E. Fattorusso, O. Taglialatela-Scafati, M.D. Rosa, and A. Ianaro Tetrahedron 55 1999 13831 13840
3. D.J. Gochfeld, and M.T. Hamann J. Nat. Prod. 64 2001 1477 1479
4. F. Rahm, P.Y. Hayes, and W. Kitching Heterocycles 64 2004 523 575
5. P.Y. Hayes, and W. Kitching J. Am. Chem. Soc. 124 2002 9718 9719
6. S. Kowashi, T. Ogamino, J. Kamei, Y. Ishikawa, and S. Nishiyama Tetrahedron Lett. 45 2004 4393 4396
7. Synthetic studies on plakortones: P.Y. Hayes, and W. Kitching Heterocycles 62 2004 173 177
8. H.K. Lee, and H.N.C. Wong Chem. Commun. 2002 2114 2115
9. M.F. Semmelhack, and P. Shanmugam Tetrahedron Lett. 41 2000 3567 3571
10. C. Bittner, A. Burgo, P.J. Murphy, C.H. Sung, and A.J. Thornhill Tetrahedron Lett. 40 1999 3455 3456
11. G.C. Paddon-Jones, N.L. Hungerford, P.Y. Hayes, and W. Kitching Org. Lett. 1 1999 1095 1097
12. M. Akiyama, Y. Isoda, M. Nishimoto, A. Kobayashi, D. Togawa, N. Hirao, A. Kuboki, and S. Ohira Tetrahedron Lett. 46 2005 7483 7485
13. E.W. Schmidt, and D.J. Faulkner Tetrahedron Lett. 37 1996 6681 6684
14. S. Ohira, K. Okai, and T. Moritani J. Chem. Soc., Chem. Commun. 1992 721 722
15. T. Shioiri, and T. Aoyama Synth. Org. Chem. Jpn. 54 1996 918 928 and references cited therein
16. Generation of aldehyde in a similar case was reported. D.P. Curran, and H. Yu Synthesis 1992 123 127
17. P.R. Blakemore, W.J. Cole, P.J. Kocienski, and A. Morley Synlett 1998 26 28
18. P.R. Blakemore J. Chem. Soc., Perkin Trans. 1 2002 2563 2585
19. 3) δ 8.4, 8.5, 11.7, 13.9, 25.5, 30.1, 30.2, 32.8, 37.6, 40.5, 43.4, 44.6, 80.8, 87.7, 97.9, 131.8, 134.2, 175.7.
20. 3) δ 11.6, 17.9, 24.5, 35.3, 38.0, 44.3, 55.4, 65.8, 127.3, 127.6, 127.8, 128.9, 129.4, 135.5, 153.2, 176.2.
21. T. Tamaru, M. Mizutani, Y. Furukawa, S. Kawamura, Z. Yoshida, K. Yanagi, and M. Minobe J. Am. Chem. Soc. 106 1984 1079 1085
22. P.A. Bartlett, K.H. Holm, and A. Morimoto J. Org. Chem. 50 1985 5179 5183
23. 3) δ 8.3, 8.6, 11.6, 13.9, 25.5, 29.7, 30.2, 31.7, 37.5, 40.8, 43.5, 46.0, 80.0, 87.7, 98.0, 131.9, 133.9, 175.6.
24. 4).
25. The sample was provided by Professor Abimael D. Rodríguez, University of Puerto Rico; M.d.S. Jiménez, S.P. Garzón, and A.D. Rodríguez J. Nat. Prod. 66 2003 655 661