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Synthesis 2007(13): 1943-1948
DOI: 10.1055/s-2007-983741
DOI: 10.1055/s-2007-983741
PAPER
© Georg Thieme Verlag Stuttgart · New York
exo-2-Oxazolidinone Dienes in the Total Synthesis of the Natural Carbazoles, 6-Methoxymurrayanine and Clausenine
Further Information
Received
21 February 2007
Publication Date:
18 June 2007 (online)
Publication History
Publication Date:
18 June 2007 (online)
Abstract
A new application of exo-2-oxazolidinone dienes in the regioselective synthesis of natural carbazoles, 6-methoxymurrayanine (6) and clausenine (7), is described. The regioselective cycloaddition of novel diene 10 to acrolein by Lewis acid catalysis provided adduct 12, which after aromatization gave benzoxazolone 14 as the key intermediate for the preparation of both carbazoles. A straightforward and efficient synthesis of 7 was carried out by a procedure with no isolation of intermediates, starting from 14 and went through a sequence of hydrogenation-hydrolysis-methylation and Pd-cyclization to give the desired carbazole 7 in high overall yield.
Key words
carbazoles - 4,5-dimethylene-2-oxazolidinone dienes - 6-methoxymurrayanine - clausenine - Diels-Alder reaction - decarbonylation
- For selected references, see:
-
1a
Knölker H.-J.Reddy KR. Chem. Rev. 2002, 102: 4303 ; and references cited therein -
1b
Chakraborty DP.Roy S. In Progress in the Chemistry of Organic Natural Products Vol. 57:Herz W.Grisebach H.Kirby GW.Tamm C. Springer; Vienna: 1991. p.71 -
1c
Fiebig M.Pezzuto JM.Soejarto DD.Kinghorn AD. Phytochemistry 1985, 24: 3041 -
1d
Chakraborty DP. Planta Med. 1980, 39: 97 -
1e
Wu T.-S.Chan Y.-Y.Liou M.-J.Lin F.-W.Shi L.-S.Chen K.-T. Phytother. Res. 1998, 12: S80 -
1f
Bringmann G.Ledermann A.Holenz J.Kao M.-T.Busse U.Wu HG.François G. Planta Med. 1998, 64: 54 -
1g
Wu T.-S.Huang S.-C.Wu P.-L.Teng C.-M. Phytochemistry 1996, 43: 133 -
1h
Chakraborty A.Chowdhury BK.Bhattacharyya P. Phytochemistry 1995, 40: 295 -
1i
Chakraborty A.Saha C.Podder G.Chowdhury BK.Bhattacharyya P. Phytochemistry 1995, 38: 787 -
1j
Bringmann G.Ledermann A.François G. Heterocycles 1995, 40: 293 -
2a
Chakraborty DP.Bhattacharyya P.Roy S.Bhattacharyya SP.Biswas AK. Phytochemistry 1978, 17: 834 -
2b
Chowdhury BK.Chakraborty DP. Chem. Ind. (London) 1969, 549 -
2c
Wu T.-S.Huang S.-C.Wu P.-L.Kuoh C.-S. Phytochemistry 1999, 52: 523 -
3a
Chakraborty DP.Barman BK.Bose PK. Tetrahedron 1965, 21: 681 -
3b
Bhattacharyya P.Chakraborty DP. Phytochemistry 1973, 12: 1831 - 4
Chowdhury BK.Chakraborty DP. Phytochemistry 1971, 10: 1967 - For selected and recent examples, see:
-
5a
Pindur U. Chimia 1990, 44: 406 ; and references cited therein -
5b
Beccalli E.Marchesini A.Pilati T. Tetrahedron 1996, 52: 3029 -
5c
Choshi T.Sada T.Fujimoto H.Nagayama C.Sugino E.Hibino S. J. Org. Chem. 1997, 62: 2535 -
5d
Lee C.-Y.Lin C.-F.Lee J.-L.Chiu C.-C.Lu W.-D.Wu M.-J. J. Org. Chem. 2004, 69: 2106 -
5e
Knölker H.-J.Schlechtingen G. Heterocycles 2004, 63: 2393 -
5f
Knölker H.-J. Curr. Org. Synth. 2004, 1: 309 -
5g
Appukkuttan P.Van der Eycken E.Dehaen W. Synlett 2005, 127 -
5h
Freeman AW.Urvoy M.Criswell ME. J. Org. Chem. 2005, 70: 5014 -
5i
Liu C.-Y.Knochel P. Org. Lett. 2005, 7: 2543 -
5j
Tsang WCP.Zheng N.Buchwald SL. J. Am. Chem. Soc. 2005, 127: 14560 -
5k
Scott TL.Yu X.Gorugantula SP.Carrero-Martínez G.Söderberg BCG. Tetrahedron 2006, 62: 10835 -
5l
Kitawaki T.Hayashi Y.Ueno A.Chida N. Tetrahedron 2006, 62: 6792 - For examples of synthesis of carbazoles 1-3, see:
-
6a
Bringmann G.Tasler S.Endress H.Peters K.Peters E.-M. Synthesis 1998, 1501 -
6b
Chakraborty DP.Chowdhury BK. J. Org. Chem. 1968, 33: 1265 -
6c
Knölker H.-J.Bauermeister M. Tetrahedron 1993, 48: 11221 -
6d
Kuwahara A.Nakano K.Nozaki K. J. Org. Chem. 2005, 70: 413 -
6e
Mal D.Senapati B.Pahari P. Tetrahedron Lett. 2006, 47: 1071 -
6f
Knölker H.-J.Wolpert M. Tetrahedron 2003, 59: 5317 -
6g
Brenna E.Fuganti C.Serra S. Tetrahedron 1998, 54: 1585 - 7
Mandal AB.Delgado F.Tamariz J. Synlett 1998, 87 -
8a
Zempoalteca A.Tamariz J. Heterocycles 2002, 57: 259 -
8b
Benavides A.Peralta J.Delgado F.Tamariz J. Synthesis 2004, 2499 -
9a
Hernández R.Sánchez JM.Gómez A.Trujillo G.Aboytes R.Zepeda G.Bates RW.Tamariz J. Heterocycles 1993, 36: 1951 -
9b
Mandal AB.Gómez A.Trujillo G.Méndez F.Jiménez HA.Rosales MJ.Martínez R.Delgado F.Tamariz J. J. Org. Chem. 1997, 62: 4105 - 10
Li W.-S.McChesney JD.El-Feraly FS. Phytochemistry 1991, 30: 343 - 11
Hamza OJM.van den Bout-van den Beukel CJP.Matee MIN.Moshi MJ.Mikx FHM.Selemani HO.Mbwambo ZH.Van der Ven AJAM.Verweij PE. J. Ethnopharmacol. 2006, 108: 124 - 12 For a preliminary report, see:
González-Romero C.Bernal P.Jiménez F.Cruz MC.Fuentes-Benites A.Benavides A.Bautista R.Tamariz J. Pure Appl. Chem. 2007, 79: 181 - 13
Fuentes A.Martínez-Palou R.Jiménez-Vázquez HA.Delgado F.Reyes A.Tamariz J. Monatsh. Chem. 2005, 136: 177 -
14a
Åkermark B.Eberson E.Jonsson E.Pettersson E. J. Org. Chem. 1975, 40: 1365 -
14b
Liu G.Zhang A. Tetrahedron Lett. 1999, 40: 341 -
15a
Smolík J.Kraus M. Collect. Czech. Chem. Commun. 1972, 37: 3042 -
15b
Demopoulos BJ.Anderson HJ.Loader CE.Faber K. Can. J. Chem. 1983, 61: 2415 -
15c
Peroutková V.Beránek L. Collect. Czech. Chem. Commun. 1976, 41: 526 -
15d
Lejemble P.Maire Y.Gaset A.Kalck P. Chem. Lett. 1983, 1403