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
Synthesis 2006(23): 4005-4012
DOI: 10.1055/s-2006-950331
DOI: 10.1055/s-2006-950331
PAPER
© Georg Thieme Verlag Stuttgart · New YorkEnantioselective Synthesis of (+)-Sedamine and (-)-Allosedamine
Further Information
Received
7 July 2006
Publication Date:
20 October 2006 (online)
Publication History
Publication Date:
20 October 2006 (online)

Abstract
Two different approaches to the enantioselective syntheses of (+)-sedamine and (-)-allosedamine are described, both using the Sharpless asymmetric epoxidation as the key step. Regioselective reduction of epoxides, chemoselective oxidation of alcohols, ring-closing metathesis, and nucleophilic displacements were the other key steps employed.
Key words
alkaloids - asymmetric synthesis - regioselective reduction - ring-closing metathesis
- 1a
Strunz GM.Findlay JA. In The Alkaloids Vol. 26:Brossi A. Academic Press; New York: 1985. p.89-174 - 1b
Numata A.Ibuka T. In The Alkaloids Vol. 31:Brossi A. Academic Press; New York: 1987. - 2a
Marion L.Lavigne R.Lemay L. Can. J. Chem. 1951, 29: 347 - 2b
Granck B. Chem. Ber. 1958, 91: 2803 - 3a
Logar S.Mesicek M.Perpar M.Seles E. Farm. Vestn. 1974, 21 ; Chem. Abstr. 1975, 82, 82916h - 3b
Krasnov EA.Petrova LV.Bekker EF. Khim. Prir. Soedin. 1977, 585 ; Chem. Abstr. 1977, 87, 164249k - 4
Schoff C.Kauffmann T.Berth P.Bundschuh W.Dummer G.Fett H.Habermehl G.Wieters E.Wust W. Liebigs Ann. Chem. 1957, 608: 88 - 5
Gershwin ME.Terr A. Clin. Rev. Allergy Immunol. 1996, 14: 241 - For the synthesis of (±)-sedamine, see:
- 6a
Tufariello JJ.Ali SA. Tetrahedron Lett. 1978, 47: 4647 - 6b
Shono T.Matsumura Y.Tsubatta K. J. Am. Chem. Soc. 1981, 103: 1172 - 6c
Tirel PJ.Vaultier M.Carrie R. Tetrahedron Lett. 1989, 30: 1947 - 6d
Pilli RA.Dias LC. Synth. Commun. 1991, 21: 2213 - 6e
Ozawa N.Nakajima S.Zzoya K.Hamaguchi F.Nagasaka T. Heterocycles 1991, 32: 889 - 6f
Driessens F.Hootele C. Can. J. Chem. 1991, 69: 211 - 6g
Ghiaci M.Adibi M. Org. Prep. Proced. Int. 1996, 38: 474 - For the synthesis of (+)- and (-)-sedamine, see:
- 7a
Beyerman HC.Eveleens W.Muller YMF. Recl. Trav. Chim. Pays-Bas 1956, 75: 63 - 7b
Beyerman HC.Eenshuistra J.Eveleens W.Zweistra A. Recl. Trav. Chim. Pays-Bas 1959, 78: 43 - 7c
Schopf C.Cummer G.Wust W. Liebigs Ann. Chem. 1959, 626: 134 - 7d
Wakabayachi T.Watanabe K.Kato Y.Saito M. Chem. Lett. 1977, 223 - 7e
Irie K.Aoe K.Tanaka T.Saito S. J. Chem. Soc., Chem. Commun. 1985, 633 - 7f
Pyne SG.Bloem P.Chapman SL.Dixon CE.Griffith R. J. Org. Chem. 1990, 55: 1086 - 7g
Kiguchi T.Nakazono Y.Kotera S.Ninomiya I.Naito T. Heterocycles 1990, 31: 1525 - 7h
Comins DL.Hong H. J. Org. Chem. 1993, 58: 5035 - 7i
Poerwono H.Higashiyama K.Takahashi H. Heterocycles 1998, 47: 263 - 7j
Yu CY.Meth-Cohn O. Tetrahedron Lett. 1999, 40: 6665 - 7k
Compere C.Marazano C.Das BC. J. Org. Chem. 1999, 64: 4528 - 7l
Cossy J.Willis C.Bellosta V.BouzBouz S. J. Org. Chem. 2002, 67: 1982 - 7m
Felpin FX.Lebreton J. J. Org. Chem. 2002, 67: 9192 - 7n
Angoli M.Barilli A.Lesma G.Passarella D.Riva S.Silvani A.Danieli B. J. Org. Chem. 2003, 68: 9525 - 7o
Zheng G.Dwoskin LP.Crooks PA. J. Org. Chem. 2004, 69: 8514 - 7p
Yadav JS.Reddy MS.Rao PP.Prasad AR. Tetrahedron Lett. 2006, 47: 4397 - For the synthesis of (±)-allosedamine, see:
- 8a
Ozawa N.Nakajima K.Zaoya K.Hamaguchi F.Nagasaka T. Heterocycles 1991, 32: 989 - 8b
Liguori A.Ottana R.Romeo G.Sindona S.Uccella N. Chem. Ber. 1989, 122: 2089 ; and references cited therein - For the synthesis of (+)- and (-)-allosedamine, see:
- 9a
Felpin F.-X.Lebreton J. Tetrahedron Lett. 2002, 43: 225 - 9b
Oppolzer W.Deeberg J.Tamura O. Helv. Chim. Acta 1994, 77: 554 - 9c
Kang B.Chang S. Tetrahedron 2004, 60: 7353 - 9d
Raghavan S.Rajender A. Tetrahedron Lett. 2004, 45: 1919 - 10
Vatele J.-M. Tetrahedron Lett. 2006, 47: 715 - 11a
Mehta G.Reddy MS.Thomas A. Tetrahedron 1998, 54: 7865 - 11b
Masaki Y.Oda H.Kozuta K.Usui A.Itoh A.Xu F. Tetrahedron Lett. 1992, 33: 5089