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Synthesis 2005(4): 527-529
DOI: 10.1055/s-2004-837305
DOI: 10.1055/s-2004-837305
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
A Total Synthesis of the Aromatic Monoterpene Espintanol
Further Information
Received
10 August 2004
Publication Date:
22 December 2004 (online)
Publication History
Publication Date:
22 December 2004 (online)
Abstract
A synthesis of the leishmanicidal and trypanocidal monoterpene espintanol from dimethyl 2-isopropyl-3-oxoglutarate and 2-butynal using a Michael addition-Dieckmann cyclization as the key step is described.
Key words
monoterpene - leishmanicidal - trypanocidal - cyclization - total synthesis
- 1
Hocquemiller R.Cortés D.Arango GJ.Myint SH.Cave A.Angelo A.Muñoz V.Fournet A. J. Nat. Prod. 1991, 54: 445 -
2a
Söderberg BC.Fields SL. Org. Prep. Proced. Int. 1996, 28: 221 -
2b
Tomooka CS.Liu H.Moore HW. J. Org. Chem. 1996, 61: 6009 -
2c
Wadsworth DJ.Losch S. Tetrahedron 1994, 50: 8673 - 3
Schmidt HS. inventors; Dynamit Nobel AG, DE OS 3136720. ; Chem. Abstr. 1983, 99, 22134 - 4
Covarrubias-Zúñiga A.San Germán-Sanchez L.Avila-Zárraga JG. Synth. Commun. 2003, 33: 3165 -
5a
Covarrubias-Zúñiga A.González-Lucas A. Tetrahedron Lett. 1998, 39: 2881 -
5b
Covarrubias-Zúñiga A.González-Lucas A.Domínguez MM. Tetrahedron 2003, 1989 -
5c
Covarrubias-Zúñiga A.Díaz-Domínguez J.Olguín-Uribe JS. Synth. Commun. 2001, 31: 1373 - 6
Perlmutter P. Conjugative Addition Reactions in Organic Synthesis Pergamon; Oxford: 1992. - 7
Schaefer JP.Bloomfield J. J. Org. React. 1967, 15: 1 - 8
Bamfield P.Gordon PF. Chem. Soc. Rev. 1984, 13: 441 - 9
Matsumoto M.Kobayashi H.Hotta Y. J. Org. Chem. 1984, 49: 4740 - 10
Covarrubias-Zúñiga A.Avila-Zárraga JG.Arias-Salas D. Synth. Commun. 2003, 33: 3173 -
11a
Cohen TR.Schambach RA. J. Am. Chem. Soc. 1970, 92: 3189 -
11b
Cairncross A.Roland JR.Henderson RM.Sheppard WA. J. Am. Chem. Soc. 1970, 92: 3187 - 12
Covarrubias-Zúñiga A.Ríos-Barrios E. J. Org. Chem. 1997, 62: 5688