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Synthesis 2008(7): 1033-1038
DOI: 10.1055/s-2008-1066985
DOI: 10.1055/s-2008-1066985
PAPER
© Georg Thieme Verlag Stuttgart · New YorkSynthesis of Sedamine by Cycloisomerisation of an Allenic Hydroxylamine
Weitere Informationen
Received
19 August 2007
Publikationsdatum:
06. März 2008 (online)
Publikationsverlauf
Publikationsdatum:
06. März 2008 (online)

Abstract
Isoxazolidines have been prepared in a stereoselective manner by treatment of allenic hydroxylamines with silver(I). This methodology has been used in a short synthesis of the alkaloid (+)-sedamine.
Key words
cyclisation - allenes - heterocycles - alkaloids - stereoselectivity
- 1
Bates RW.Sa-Ei K. Org. Lett. 2002, 4: 4225 - 2
Knapp S. Chem. Soc. Rev. 1999, 28: 61 - 3a
Claesson A.Sahlberg C.Luthman K. Acta Chem. Scand. 1979, 33B: 309 - 3b
Claesson A.Olsson L.-I. Synthesis 1979, 743 - 3c
Arseniyadis S.Gore J. Tetrahedron Lett. 1983, 24: 3997 - 3d
Arseniyadis S.Sartoretti J. Tetrahedron Lett. 1985, 26: 729 - 3e
Lathbury DC.Shaw RW.Bates PA.Hursthouse MB.Gallagher T. J. Chem. Soc., Perkin Trans. 1 1989, 2415 - 3f
Marshall JA.Sehon CA. J. Org. Chem. 1995, 60: 5966 - 3g
Amombo MO.Hausherr A.Reissig H.-U. Synlett 1999, 1871 - 3h
Kaden S.Reissig H.-U.Brüdgam I.Hartl H. Synthesis 2006, 1351 - 3i
Chowdhury MA.Reissig H.-U. Synlett 2006, 2383 - 3j For a review of allene cyclisation, see:
Bates RW.Satchareon V. Chem. Soc. Rev. 2002, 31: 12 - 4a For recent syntheses, see:
Bates RW.Sa-Ei K. Tetrahedron 2002, 58: 5957 - 4b
Fustero S.Jimenez D.Moscardo J.Catalan S.del Pozo C. Org. Lett. 2007, 9: 5283 - 4c
Yadav JS.Sridar Reddy M.Purushothama Rao P.Prasad AR. Tetrahedron Lett. 2006, 47: 4397 - 4d
Borah JC.Boruwa J.Barua NC. Lett. Org. Chem. 2006, 3: 140 - 4e
Zheng G.Dwoskin LP.Crooks PA. J. Org. Chem. 2004, 69: 8514 - 4f
Josephson NS.Snapper ML.Hoveyda AH. J. Am. Chem. Soc. 2004, 126: 3734 - 4g
Angoli M.Barilli A.Lesma G.Passarella D.Riva S.Silvani A.Danieli B. J. Org. Chem. 2003, 68: 9525 - 4h
Felpin F.-X.Lebreton J. J. Org. Chem. 2002, 67: 9192 - 4i
Cossy J.Willis C.Bellosta V.BouzBouz S. J. Org. Chem. 2002, 67: 1982 - 5
Meth-Cohn O,Yu C.-Y,Lestage P,Lebrun M.-C,Cagniard D.-H, andRenard P. inventors; European Patent 1050531.MissingFormLabel - 6a
Grochowski E.Jurczak J. Synthesis 1976, 682 - 6b
Iwagami H.Yatagai M.Nakazawa M.Orita H.Honda Y.Ohnuki T.Yukawa T. Bull. Chem. Soc. Jpn. 1991, 64: 175 - 7a The alkynol precursor for allene 4 was prepared by a modification of Lansbury and Pattison:
Lansbury PT.Pattison VA. J. Am. Chem. Soc. 1962, 84: 4295 - 7b See also:
Hommes H.Verkruijsse HD.Brandsma L. Recl. Trav. Chim. Pays-Bas 1980, 99: 113 - 7c
For the allenol precursor for allene 5, see ref. 9.
- 8a
Arcadi A.di Giuseppe S. Curr. Org. Chem. 2004, 8: 795 - 8b
Hoffmann-Röder A.Krause N. Org. Biomol. Chem. 2005, 3: 387 - 8c
Hyland CJT.Hegedus LS. J. Org. Chem. 2006, 71: 8658 - 8d
Zhang Z.Widenhoefer RA. Angew. Chem. Int. Ed. 2007, 46: 283 - 8e
Yeom H.-S.Lee E.-S.Shin S. Synlett 2007, 2292 - 9a For ring-opening with lithium acetylide, see:
Brandsma L. Preparative Acetylenic Chemistry 2nd ed.: Elsevier; Amsterdam: 1988. p.67 - 9b For allene formation, see:
Searles S.Li Y.Nassim B.Lopes M.-TR.Tran PT.Crabbé P. J. Chem. Soc., Perkin Trans 1 1984, 747 - 10a
Felpin F.-X.LeBreton J. Eur. J. Org. Chem. 2003, 3693 - 10b
Phillips AJ.Abell AD. Aldrichimica Acta 1999, 32: 75 - 11
Fu GC.Nguyen ST.Grubbs RH. J. Am. Chem. Soc. 1993, 115: 9856MissingFormLabel - 13
Czech BP.Bartsch RA. J. Org. Chem. 1984, 49: 4076 - 14
Poerwono H.Hagashiyama K.Takahashi H. Heterocycles 1998, 47: 262
References
Cossy et al. also employed RCM to form the piperidine ring, but at a different position, see ref. 4i.