Effect of allylic and homoallylic substituents on cross metathesis: syntheses of prostaglandins F2α and J2

Tetrahedron Letters

Volumn 47, Issue 37, 2006, Pages 6689-6693

  Sheddan, Neil A ^a   Arion, Vladimir B ^a   Mulzer, Johann ^a  

^a Institut fur Organische Chemie   (Austria)

Author keywords

Cross metathesis; Natural products; Prostaglandin; Total synthesis

Indexed keywords

ALLYL COMPOUND; LACTONE; PROSTAGLANDIN F2 ALPHA; PROSTAGLANDIN J2;

ALLYLIC REARRANGEMENT; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROSTAGLANDIN SYNTHESIS; REACTION ANALYSIS; RING CLOSING METATHESIS; STRUCTURE ANALYSIS;

EID: 33746823313     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.06.140     Document Type: Article

References (27)

1. For lead references and recent reviews see:. Noyori R., and Suzuki M. Science 259 (1993) 44-45
2. Sugrue M.F. J. Med. Chem. 40 (1997) 2793-2809
3. Clark A.F. Emerging Drugs 4 (1999) 333-353
4. Maruyama T., Kuwabe S.-I., Kawanaka Y., Shiraishi T., Shinagawa Y., Sakata K., Seki A., Kishida Y., Yoshida H., Maruyama T., Ohuchida S., Nakai H., Hashimoto S., Kawamura M., Kondo K., and Toda M. Bioorg. Med. Chem. 10 (2002) 2103-2110
5. Komoto J., Yamada T., Watanabe K., Woodward D.F., and Takusagawa F. Biochemistry 45 (2006) 1987-1996 and references therein
6. For a recent review, see:. Collins P.W., and Djuric S.W. Chem. Rev. 93 (1993) 1533-1564
7. Morrow J.D., Awad J.A., Boss H.J., Blair I.A., and Roberts II L.J. Proc. Natl. Acad. Sci. U.S.A. 89 (1992) 10721-10725
8. Roberts II L.J., Montine T.J., Markesbery W.R., Tapper A.R., Hardy P., Chemtob S., Dettbarn W.D., and Morrow J.D. J. Biol. Chem. 273 (1998) 13605-13612 and references therein
9. Klimko, P. G.; Bishop, J.; Desantis Jr., L.; Sallee, V. L., EP 639563 A2 950222, US 93-101598 930803.
10. For recent reviews on cross metathesis, see:. Chatterjee A.K., Choi T.-L., Sanders D.P., and Grubbs R.H. J. Am. Chem. Soc. 125 (2003) 11360-11370
11. Van de Weghe P., Eustache J., and Cossy J. Curr. Topics Med. Chem. 5 (2005) 1461-1472
12. Prunet J. Curr. Topics Med. Chem. 5 (2005) 1559-1577
13. Sheddan N.A., and Mulzer J. Org. Lett. 8 (2006) 3101-3104
14. Jacobo S.H., Chang C.-T., Lee G.-J., Lawson J.A., Powell W.S., Pratico D., FitzGerald G.A., and Rokach J. J. Org. Chem. 71 (2006) 1370-1379
15. Fleming I., and Winter S.B.D. J. Chem. Soc., Perkin Trans. 1 (1998) 2687-2700
16. For the effects of allylic and homoallylic substituents on metathesis see (and references cited therein);. Castoldi D., Caggiano L., Bayón P., Costa A.M., Cappella P., Sharon O., and Gennari C. Tetrahedron 61 (2005) 2123-2139
17. Caggiano L., Castoldi D., Beumer R., Bayón P., Telser J., and Gennari C. Tetrahedron Lett. 44 (2003) 7913-7919
18. McNaughton B.R., Bucholtz K.M., Camaanõ-Moure A., and Miller B.L. Org. Lett. 7 (2005) 733-736
19. Kawaguchi T., Funamori N., Matsuya Y., and Nemoto H. J. Org. Chem. 69 (2004) 505-509
20. BouzBouz S., and Cossy J. Org. Lett. 3 (2001) 1451-1454
21. BouzBouz S., Simmons R., and Cossy J. Org. Lett. 6 (2004) 3465-3467
22. Farrugia L.J. J. Appl. Cryst. 30 (1997) 565
23. max 50°, wR (all 3038 data) 0.1898, conventional R (2521 data with I > 2σ(I)) 0.0631. Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 602481 and 602482, respectively. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk].
24. 2: 496.3404; found 496.3395; -19.2 (c = 0.43, acetone).
25. 13C and optical rotation are concurrent with literature values. Parve O., Jarving I., Martin I., Metsala A., Vallikivi I., Aidnik M., Pehk T., and Samel N. Bioorg. Med. Chem. Lett. 9 (1999) 1853-1858
26. Sato Y., Takimoto M., and Mori M. Chem. Pharm. Bull. 48 (2000) 1753-1760
27. Zanoni G., Porta A., De Toma Q., Castronova F., and Vidari G. J. Org. Chem. 68 (2003) 6437-6439