RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2008(18): 2939-2942
DOI: 10.1055/s-2008-1067218
DOI: 10.1055/s-2008-1067218
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Asymmetric Synthesis of (-)-6-epi-Centrolobine
Weitere Informationen
Received
14 May 2008
Publikationsdatum:
06. August 2008 (online)
Publikationsverlauf
Publikationsdatum:
06. August 2008 (online)
Abstract
A stereoselective total synthesis of (-)-6-epi-centrolobine, an unnatural analogue of (-)-centrolobine, starting from readily available tri-O-acetyl-d-glucal has been described for the first time. The key steps involved in this synthetic approach are stereoselective C-glycosidation, dehydroxylation and Wittig reaction. The target molecule was achieved in nine steps with 49% overall yield.
Key words
centrolobine - tri-O-acetyl-d-glucal - C-glycosidation - dehydroxylation - Wittig reaction
-
1a
de Albuquerque IL.Galeffi C.Casinovi CG.Marini-Bettolo GB. Gazz. Chim. Ital. 1964, 94: 287 -
1b
Galeffi C.Giulio Casinovi C.Marini-Bettolo GB. Gazz. Chim. Ital. 1965, 95: 95 -
1c
Craveiro AA.Prado AdC.Gottlieb OR.Welerson de Albuquerque PC. Phytochemistry 1970, 9: 1869 - 2
Araujo CAC.Alefrio LV.Leon LL. Phytochemistry 1998, 49: 751 - 3
Colobert F.Mazery RD.Solladie G.Carreno MC. Org. Lett. 2002, 4: 1723 -
4a
Marumoto S.Jaber JJ.Vitale JP.Rychnovsky SD. Org. Lett. 2002, 4: 3919 -
4b
Carreno MC.Mazery RD.Urbano A.Colobert F.Solladie G. J. Org. Chem. 2003, 68: 7779 -
4c
Evans PA.Cui J.Gharpure SJ. Org. Lett. 2003, 5: 3883 -
4d
Lee E.Kim HJ.Jang WS. Bull. Korean Chem. Soc. 2004, 25: 1609 -
4e
Boulad L.BouzzBouz S.Cossy J.Franck X.Figadère B. Tetrahedron Lett. 2004, 45: 6603 -
4f
Clarke PA.Martin WHC. Tetrahedron Lett. 2004, 45: 9061 -
4g
Chan KP.Loh TP. Org. Lett. 2005, 61: 4491 -
4h
Clarke PA.Martin WHC. Tetrahedron 2005, 61: 5433 -
4i
Jennings MP.Clemens RT. Tetrahedron Lett. 2005, 46: 2021 -
4j
Bohrsch V.Blechert S. Chem. Commun. 2006, 1968 -
4k
Lee CHA.Loh TP. Tetrahedron Lett. 2006, 47: 1641 -
4l
Prasad KR.Anbarasan P. Tetrahedron 2007, 63: 1089 -
4m
Washio T.Yamaguchi R.Abe T.Nambu H.Anada M.Hashimolo S. Tetrahedron 2007, 63: 12037 -
4n
Dziedzic M.Furman B. Tetrahedron Lett. 2008, 49: 678 - 5
Chandrasekhar S.Prakash SJ.Shyamsunder T. Tetrahedron Lett. 2005, 46: 6651 - 6
Ramnauth J.Poulin O.Rakhit S.Maddaford SP. Org. Lett. 2001, 3: 2013
References
4-Benzyloxybenzyl triphenylphosphonium
bromide was prepared in two steps from commercially available
p-benzyloxybenzyl alcohol using a known
protocol, see ref. 4b.