Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2006(17): 2807-2811
DOI: 10.1055/s-2006-950274
DOI: 10.1055/s-2006-950274
LETTER
© Georg Thieme Verlag Stuttgart · New Yorkα-EWG-Substituted Enones: Suitable Substrates for Ring-Closing Metathesis
Further Information
Received
13 July 2006
Publication Date:
09 October 2006 (online)
Publication History
Publication Date:
09 October 2006 (online)
Abstract
The A-ring of hexacyclinic acid has been synthesised, using a ring-closing metathesis involving an α-EWG-substituted enone as the key step. We have then explored the scope of this reaction, which gives access to various 5- and 6-membered rings.
Key words
metathesis - ring-closure - enones - natural products
- 1
Höfs R.Walker M.Zeeck A. Angew. Chem. Int. Ed. 2000, 39: 3258 - 2a
Sato B.Muramatsu H.Miyauchi M.Hori Y.Hino M.Hashimoto S.Terano H. J. Antibiot. 2000, 53: 123 - 2b
Sato B.Nakajima H.Miyauchi M.Hori Y.Hashimoto S.Terano H. J. Antibiot. 2000, 53: 204 - 2c
Yoshimura S.Sato B.Miyauchi M.Kinoshita T.Takase S.Terano H. J. Antibiot. 2000, 53: 615 - 3a A-ring:
Funel J.-A.Prunet J. J. Org. Chem. 2004, 69: 4555 - 3b AB-rings:
Suzuki T.Nakada M. Tetrahedron Lett. 2002, 43: 3263 - ABC-rings:
- 3c
Methot JL.Roush WR. Org. Lett. 2003, 5: 4223 - 3d
Armstrong A.Goldberg FW.Sandham DA. Tetrahedron Lett. 2001, 42: 4585 - 3e
Funel J.-A.Prunet J. Chem. Commun. 2005, 4833 - DEF-rings:
- 3f
Clarke P.Davie R.Peace S. Tetrahedron Lett. 2004, 45: 927 - 3g
Clarke P.Davie R.Peace S. Tetrahedron 2005, 61: 2335 - 4a
Starr JT.Evans DA. Angew. Chem. Int. Ed. 2002, 41: 1787 - 4b
Evans DA.Starr JT. J. Am. Chem. Soc. 2003, 125: 13531 - 4c
Vosburg DA.Vanderwal CD.Sorensen EJ. J. Am. Chem. Soc. 2002, 124: 4552 - 4d
Vanderwal CD.Vosburg DA.Weiler S.Sorensen EJ. J. Am. Chem. Soc. 2003, 125: 5393 - AB-ring system:
- 5a
Clarke P.Cridland A. Org. Lett. 2005, 7: 4221 - DEF-ring system:
- 5b
Clarke P.Grist M.Ebden M.Wilson C.Blake AJ. Tetrahedron 2005, 61: 353 - 5c
Clarke P.Grist M.Ebden M.Wilson C. Chem. Commun. 2003, 1560 - 6
James P.Felpin F.-X.Landais Y. J. Org. Chem. 2005, 70: 7985 - 7
Stellfeld T.Bhatt U.Kalesse M. Org. Lett. 2004, 6: 3889 - For representative examples of use of α-carbalkoxycyclo-enones in total synthesis, see:
- 8a
Liu H.-J.Shia K.-S. Tetrahedron 1998, 54: 13449 - 8b
Liu H.-J.Tran DD.-P. Tetrahedron Lett. 1999, 40: 3827 - 8c
Zhu J.-L.Shia K.-S.Liu H.-J. Chem. Commun. 2000, 1599 - For re-presentative examples of use of α-carboxylactones in total synthesis, see:
- 8d
Hoye TR.Caruso AJ.Magee AS. J. Org. Chem. 1982, 47: 4152 - 8e
Horne DA.Fugmann B.Yakushijin K.Büchi G. J. Org. Chem. 1993, 58: 62 - 8f
Ishihara J.Sugimoto T.Murai A. Tetrahedron 1997, 53: 16029 - For representative examples of use of α-carboxylactams in total synthesis, see:
- 8g
Vedejs E.Campbell JB.Gadwood RC.Rodgers JD.Spear KL.Watanabe Y. J. Org. Chem. 1982, 47: 1534 - 8h
Vedejs E.Reid JG.Rodgers JD.Wittenberger SJ. J. Am. Chem. Soc. 1990, 112: 4351 - 8i
Vedejs E.Wittenberger SJ. J. Am. Chem. Soc. 1990, 112: 4357 - 8j
Thomas EJ.Watts JP. J. Chem. Soc., Chem. Commun. 1990, 464 - 8k
Thomas EJ.Watts JP. J. Chem. Soc., Chem. Commun. 1990, 467 - 8l
Ackermann J.Matthes M.Tamm C. Helv. Chim. Acta 1990, 73: 122 - 8m
Merifield E.Thomas EJ. J. Chem. Soc., Perkin Trans. 1 1999, 3269 - 8n
Vedejs E.Duncan SM. J. Org. Chem. 2000, 65: 6073 - 9 Rhodium carbene cyclisation:
Yakura T.Ueki A.Kitamura T.Tarraka K.Nameki M.Ikeda M. Tetrahedron 1999, 55: 7461 - Intramolecular Knoevenagel condensation:
- 10a
Kato M.Kamat VP.Yoshikoshi A. Synthesis 1988, 699 - 10b
Funk RL.Fitzgerald JF.Olmstead TA.Para KS.Wos JA. J. Am. Chem. Soc. 1993, 115: 8849 - 11
Souza FES.Sutherland HS.Carlini R.Rodrigo R. J. Org. Chem. 2002, 67: 6568 - For representative examples of formation of rings bearing a conjugated exo-ester via RCM, see:
- 12a
Kirkland TA.Grubbs RH. J. Org. Chem. 1997, 62: 7310 - 12b
Chatterjee AK.Morgan JP.Scholl M.Grubbs RH. J. Am. Chem. Soc. 2000, 122: 3783 - 12c
Hekking KFW.Van Deft FL.Rutjes FPJT. Tetrahedron 2003, 59: 6751 - 12d
Thorstensson F.Kvarnström I.Musil D.Nilsson I.Samuelsson B. J. Med. Chem. 2003, 46: 1165 - 12e
Grigg R.Hodgson A.Morris J.Sridharan V. Tetrahedron Lett. 2003, 44: 1023 - 12f
Grigg R.Hodgson A.Morris J.Sridharan V. Tetrahedron Lett. 2003, 44: 4899 - 12g
Kim JM.Lee KY.Lee S.Kim JN. Tetrahedron Lett. 2004, 45: 2805 - 12h
Declerck V.Ribière P.Martinez J.Lamaty F. J. Org. Chem. 2004, 69: 8372 - 12i
Lee MJ.Lee KY.Lee JY.Kim JN. Org. Lett. 2004, 6: 3313 - 12j
Krishna PR.Narsingam M.Kannan V. Tetrahedron Lett. 2004, 45: 4773 - 12k
Krafft ME.Song E.-H.Davoile RJ. Tetrahedron Lett. 2005, 46: 6359 - 12l
Lee KY.Gowrisankar S.Kim JN. Bull. Korean Chem. Soc. 2005, 26: 1481 - For recent examples of butenolide formation, see:
- 12m
Crimmins MT.Zhang Y.Diaz FA. Org. Lett. 2006, 8: 2369 - 12n
Bassetti M.D’annibale A.Fanfoni A.Minissi F. Org. Lett. 2005, 7: 1805 - 13a
Crimmins MT.Chaudhary K. Org. Lett. 2000, 2: 775 - 13b
Crimmins MT.King BW.Tabet EA.Chaudhary K. J. Org. Chem. 2001, 66: 894 - 13c
Crimmins MT.Chaudhary K. J. Am. Chem. Soc. 2005, 127: 13810 - 14
Holmquist CR.Roskamp EJ. J. Org. Chem. 1989, 54: 3258 - 15
Antonioletti R.Bovicelli P.Malancara S. Tetrahedron 2002, 58: 589 - 16
Scholl M.Ding S.Lee CW.Grubbs RH. Org. Lett. 1999, 1: 953 - 17
Langer P.Eckardt T.Stoll M. Org. Lett. 2000, 2: 2991 - 18
Lawrence NJ.Crump JP.McGown AT.Hadfield JA. Tetrahedron Lett. 2001, 42: 3939 - 19a
Clemens RJ.Hyatt JA. J. Org. Chem. 1985, 50: 2431 - 19b
Skerry PS.Swain NA.Harrowven DC.Smyth D.Bruton G.Brown RCD. Chem. Commun. 2004, 1772 - 19c
Cook GR.Sun L. Org. Lett. 2004, 6: 2481 - 20
Hayakawa K.Yodo M.Kanematsu K. J. Am. Chem. Soc. 1984, 106: 6735 - 21
Ghosh AK.Cappiello J.Shin D. Tetrahedron Lett. 1998, 39: 4651