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-00000084.xml
Download PDF
Synthesis 2008(17): 2771-2775
DOI: 10.1055/s-2008-1067204
DOI: 10.1055/s-2008-1067204
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkStrategy for the Assembly of Chiral Bicyclic Lactams: A Concise Synthetic Route to (-)-Coniceine
Further Information
Received
23 April 2008
Publication Date:
24 July 2008 (online)
Publication History
Publication Date:
24 July 2008 (online)
Abstract
A concise asymmetric synthesis of chiral bicyclic lactams combining a highly stereoselective 1,2-addition on SAMP hydrazones with a ring closure metathesis has been achieved. The synthetic utility of this approach has been emphasized by the total synthesis of (-)-coniceine in high enantiomeric excess.
Key words
alkaloids - lactams - metathesis - ring closure - stereoselectivity
- For reviews on indolizidine alkaloids, see:
- 1a
Franklin AS.Overman LE. Chem. Rev. 1996, 96: 502MissingFormLabel - 1b
Michael JP. Nat. Prod. Rep. 1999, 16: 675MissingFormLabel - 1c
Michael JP. Nat. Prod. Rep. 2005, 22: 603MissingFormLabel - 2a
Brooke P.Harris DJ.Longmore RB. J. Agric. Food Chem. 1996, 44: 2129MissingFormLabel - 2b
Daly JW. Alkaloids: Chemical and Biological Perspectives Vol. 10:Pelletier SW. Pergamon; Oxford: 1996. p.155-299MissingFormLabel - 3
Roberts MF.Brown RT. Phytochemistry 1981, 20: 447 - For some recent examples, see:
- 4a
Burnett DA.Choi J.-K.Hart DJ.Tsai Y.-M. J. Am. Chem. Soc. 1984, 106: 8201MissingFormLabel - 4b
Pearson WH.Lin K.-C. Tetrahedron Lett. 1990, 31: 7571MissingFormLabel - 4c
Martin-Lopez MJ.Bermejo-Gonzales F. Tetrahedron Lett. 1994, 35: 4235MissingFormLabel - 4d
Jung ME.Choi YM. J. Org. Chem. 1991, 56: 6729MissingFormLabel - 4e
D’hooghe M.De Kimpe R. Tetrahedron 2003, 59: 3099MissingFormLabel - 5a
Hua DH.Bharathi SN.Takusagawa F.Tsujimoto T.Panangadan JAK.Hung MH.Bravo AA.Erpelding AM. J. Org. Chem. 1989, 54: 5659MissingFormLabel - 5b
Hua DH.Bharathi SN.Panangadan JAK.Tsujimoto A. J. Org. Chem. 1991, 56: 6998MissingFormLabel - 5c
Sato Y.Nukui S.Sodeoka M.Shibasaki M. Tetrahedron 1994, 50: 371MissingFormLabel - 5d
Nukui S.Sodeoka M.Shibasaki M. Tetrahedron Lett. 1993, 34: 4965MissingFormLabel - 5e
Costa A.Nájera C.Sansano JM. Tetrahedron: Asymmetry 2001, 12: 2205MissingFormLabel - 5f
Yoda H.Katoh H.Ujihara Y.Takabe K. Tetrahedron Lett. 2001, 42: 2509MissingFormLabel - 5g
Arai Y.Kontani T.Koizumi T. Chem. Lett. 1991, 2135MissingFormLabel - 5h
Waldmann H.Braun M. J. Org. Chem. 1992, 57: 4444MissingFormLabel - 5i
Davies SB.McKervey MA. Tetrahedron Lett. 1999, 40: 1229MissingFormLabel - 5j
Sánchez-Sancho F.Herradón B. Tetrahedron: Asymmetry 1998, 9: 1951MissingFormLabel - 5k
Park SH.Kang HJ.Ko S.Park S.Chang S. Tetrahedron: Asymmetry 2001, 12: 2621MissingFormLabel - 5l
Arisawa M.Takahashi M.Takezawa E.Yamaguchi T.Torisawa Y.Nishida A.Nakagawa M. Chem. Pharm. Bull. 2000, 48: 1593MissingFormLabel - 5m
Michael D.Groaning MD.Meyers AI. Chem. Commun. 2000, 1027MissingFormLabel - 6a
Hjelmgaard T.Gardette D.Tanner D.Aitken DJ. Tetrahedron: Asymmetry 2007, 18: 671MissingFormLabel - 6b
Dieter RK.Chen N.Watson RT. Tetrahedron 2005, 61: 3221MissingFormLabel - 6c
Sibi MP.Christensen JW. J. Org. Chem. 1999, 64: 6434MissingFormLabel - 6d
Takahata H.Kubota M.Takahashi S.Momose T. Tetrahedron: Asymmetry 1996, 7: 3047MissingFormLabel - 6e
Andrés JM.Herráiz-Sierra I.Pedrosa R.Pérez-Encabo A. Eur. J. Org. Chem. 2000, 1719MissingFormLabel - 6f
Michael J.Munchhof MJ.Meyers AI. J. Org. Chem. 1995, 60: 7084MissingFormLabel - 7
Job A.Janeck CF.Bettray W.Peters R.Enders D. Tetrahedron 2002, 58: 2253 - 8
Tamaru Y.Harada T.Nishi S.Yoshida Z. Tetrahedron Lett. 1982, 23: 2383 - 9a
Pandit UK.Overkleeft HS.Borer BC.Bieräugel H. Eur. J. Org. Chem. 1999, 959MissingFormLabel - 9b
Felpin F.-X.Lebreton J. Eur. J. Org. Chem. 2003, 3693MissingFormLabel - 9c
Dieters A.Martin SF. Chem. Rev. 2004, 104: 2199MissingFormLabel - 9d
Lebrun S.Couture A.Deniau E.Grandclaudon P. Org. Lett. 2007, 9: 2473MissingFormLabel - 10a
Fernández R.Ferrete A.Lassaletta JM.Llera JM.Monge A. Angew. Chem. Int. Ed. 2000, 39: 2893MissingFormLabel - 10b
Fernández R.Ferrete A.Lassaletta JM.Llera JM.Martín-Zamora E. Angew. Chem. Int. Ed. 2002, 41: 831MissingFormLabel - 10c
Fernández R.Ferrete A.Llera JM.Magriz A.Martín-Zamora E.Díez E.Lassaletta JM. Chem. Eur. J. 2004, 10: 737MissingFormLabel - 11
Lim SH.Ma S.Beak P. J. Org. Chem. 2001, 66: 9056 - 12
Ringdahl B.Pinder AR.Pereira WE.Oppenheimer NJ.Craig JC. J. Chem. Soc., Perkin Trans. 1 1984, 1 - 13
Crimmins MT.DeBaillie AC. J. Am. Chem. Soc. 2006, 128: 4936 - 14
Pihko PM.Aho JE. Org. Lett. 2004, 6: 3849