Synthesis of the ABC-ring models of goniodomin A: preference for the unnatural configuration at C11 of the BC-ring in a non-macrocyclic model system

Tetrahedron Letters

Volumn 49, Issue 20, 2008, Pages 3242-3247

  Katagiri, Takahiro ^a   Fujiwara, Kenshu ^a   Kawai, Hidetoshi ^a,b   Suzuki, Takanori ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GONIODOMIN A;

ARTICLE; CHEMICAL REACTION; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

EID: 41949100145     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.03.082     Document Type: Article

References (24)

1. Murakami M., Makabe K., Yamaguchi K., Konosu S., and Wälchli M.R. Tetrahedron Lett. 29 (1988) 1149
2. Hsia M.H., Morton S.L., Smith L.L., Beauchesne K.R., Huncik K.M., and Moeller P.D.R. Harmful Algae 5 (2006) 290
3. For bioactivity of 1:. Abe M., Inoue D., Matsunaga K., Ohizumi Y., Ueda H., Asano T., Murakami M., and Sato Y. J. Cell. Physiol. 190 (2002) 109 and references cited therein
4. Fujiwara K., Naka J., Katagiri T., Sato D., Kawai H., and Suzuki T. Bull. Chem. Soc. Jpn. 80 (2007) 1173
5. Katagiri T., Fujiwara K., Kawai H., and Suzuki T. Tetrahedron Lett. 49 (2008) 233
6. Takeda Y., Shi J., Oikawa M., and Sasaki M. Org. Lett. 10 (2008) 1013
7. Okude Y., Hirano S., Hiyama T., and Nozaki H. J. Am. Chem. Soc. 99 (1977) 3179
8. Takai K., Kimura K., Kuroda T., Hiyama T., and Nozaki H. Tetrahedron Lett. 24 (1983) 5281
9. Jin H., Uenishi J., Christ W.J., and Kishi Y. J. Am. Chem. Soc. 108 (1986) 5644
10. Nicolaou K.C., Li Y., Fylaktakidou K.C., Mitchell H.J., Wei H.-X., and Weyershausen B. Angew. Chem., Int. Ed 40 (2001) 3849
11. Sharma S., and Oehlschlager A.C. J. Org. Chem. 54 (1989) 5064
12. Murakami N., Sugimoto M., Nakajima T., Kawanishi M., Tsutsui Y., and Kobayashi M. Bioorg. Med. Chem. 8 (2000) 2651
13. Dess D.B., and Martin J.C. J. Org. Chem. 48 (1983) 4155
14. Corey E.J., and Fuchs P.L. Tetrahedron Lett. 13 (1972) 3769
15. Oka T., and Murai A. Tetrahedron 54 (1998) 1
16. Ley S.V., Norman J., Griffith W.P., and Marsden S.P. Synthesis (1994) 639
17. The stereochemistry at C7 of 23 was determined to be S by modified Mosher's method:. Ohtani I., Kusumi T., Kashman Y., and Kakisawa H. J. Am. Chem. Soc. 113 (1991) 4092
18. Origin of the stereoselectivity is unclear: cf.:. Heathcock C.H., McLaughlin M., Medina J., Hubbs J.L., Wallace G.A., Scott R., Claffey M.M., Hayes C.J., and Ott G.R. J. Am. Chem. Soc. 125 (2003) 12844
19. Miranda L.S.M., Meireles B.A., Costa J.S., Pereira V.L.P., and Vasconcellos M.L.A.A. Synlett (2005) 869
20. Smith III A.B., Cho Y.S., and Friestad G.K. Tetrahedron Lett. 39 (1998) 876
21. Sonogashira K., Tohda Y., and Hagiwara N. Tetrahedron Lett. 50 (1975) 4467
22. Higashibayashi S., Shinko K., Ishizu T., Hashimoto K., Shirahama H., and Nakata M. Synlett (2000) 1306
23. Katsuki T., and Sharpless K.B. J. Am. Chem. Soc. 102 (1980) 5974
24. H9-H10b to 3, which suggests the B-ring of 1 does not have a distorted conformation. Therefore, it was thought that 1 possesses the same stereochemical relationship between the A- and B-rings as 3 even within the macrolide framework. This conclusion is now supported by the absolute stereochemistry of 1 proposed by Sasaki.