Synthesis of (±)-lauthisan

Heterocycles

Volumn 74, Issue C, 2007, Pages 185-189

  Miyakoshi, Naoki ^a   Ohgaki, Yuki ^a   Masui, Kosuke ^a   Mukai, Chisato ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 40749114805     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-07-s(w)46     Document Type: Article

References (29)

1. Mukai C., Ukon R., and Kuroda N. Tetrahedron Lett. 44 (2003) 1583
2. Mukai C., Kobayashi M., Kubota S., Takahashi Y., and Kitagaki S. J. Org. Chem. 69 (2004) 2128
3. Mukai C., Kuroda N., Ukon R., and Itoh R. J. Org. Chem. 70 (2005) 6282
4. Mukai C., and Takahashi Y. Org. Lett. 7 (2005) 5793
5. Kuroda N., Takahashi Y., Yoshinaga K., and Mukai C. Org. Lett. 8 (2006) 1843
6. Kitagaki S., Teramoto S., and Mukai C. Org. Lett, 9 (2007) 2549
7. Mukai C., Yamashita H., and Hanaoka M. Org. Lett. 3 (2001) 3385
8. Mukai C., Ohta M., Yamashita H., and Kitagaki S. J. Org. Chem. 69 (2004) 6867
9. Kitagaki S., Shibata D., and Mukai C. Tetrahedron Lett. 48 (2007) 1735
10. For synthesis of lauthisan, see. Carling R.W., and Holmes A.B. J. Chem. Soc., Chem. Commun. (1986) 565
11. Kotsuki H., Ushio Y., Kadota I., and Ochi M. J. Org. Chem. 54 (1989) 5153
12. Tsushima K., and Murai A. Chem. Lett. (1990) 761
13. Nicolaou K.C., McGarry D.G., Somers P.K., Kim B.H., Ogilvie W.W., Yiannikouros G., Prasad C.V.C., Veale C.A., and Hark R.R. J. Am. Chem. Soc. 112 (1990) 6263
14. Paquette L.A., and Sweeney T.J. J. Org. Chem. 55 (1990) 1703
15. Udding J.U., Giesselink J.P.M., Hiemstra H., and Speckamp N. J. Org. Chem. 59 (1994) 6671
16. Kim H., Ziani-Cherif C., Oh J., and Cha J.K. J. Org. Chem. 60 (1995) 792
17. Suh Y.-G., Koo B.-A., Kim E.-N., and Choi N.-S. Tetrahedron Lett. 36 (1995) 2089
18. Coster M.J., and De Voss J.J. Org. Lett. 4 (2002) 3047
19. Rhee H.J., Beom Y., and Kim H.-K. Tetrahedron Lett. 45 (2004) 8019
20. Carrefio M.C., Des Mazery R., Urbano A., Colobert F., and Solladie G. Org. Lett. 7 (2005) 2039
21. Ortega N., Martfn T., and Martin V.S. Org. Lett. 8 (2006) 871
22. The stereochemistry of exo-5 was determined by NMR spectral consideration.
23. Ames D.E., and Davison G.M.R. Chem. Phys. Lipids 13 (1974) 223
24. Compounds 8 and 9 must be a mixture of two diastereoisomers judging from the reaction conditions used. However, their 1H and 13C NMR spectra appeared as if they were a single isomer.
25. Compound 10 was obtained as a single isomer. The (E)-stereochemistry was tentatively determined by comparison with the related compounds, although the relative stereochemistry of two chiral centers was not determined yet.
26. Luker T., and Withby R.J. Tetrahedron Lett. 37 (1996) 7661
27. Zhao Y., and Quayle P. Tetrahedron Lett. 35 (1994) 4179
28. The structure of synthetic lauthisan was confirmed by comparison with spectral data in the literatures.
29. The stereoselective reduction of 10 might be rationalized in terms of the attack of the hydride species from the sterically less hindered face (α-face) on the basis of the literature precedent.