Asymmetric Synthesis of (-)-6-epi-Centrolobine

Chada Raji Reddy; Pasupulety Phani Madhavi; Srivari Chandrasekhar

doi:10.1055/s-2008-1067218

PAPER

Asymmetric Synthesis of (-)-6-epi-Centrolobine

Chada Raji Reddy*, Pasupulety Phani Madhavi, Srivari Chandrasekhar
Organic Division - I, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160512; e-Mail: rajireddy@iict.res.in ;

Abstract

All articles of this category

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

Full Text

References

<A NAME="RZ11108SS-1A">1a</A> de Albuquerque IL. Galeffi C. Casinovi CG. Marini-Bettolo GB. Gazz. Chim. Ital. 1964, 94: 287

<A NAME="RZ11108SS-1B">1b</A> Galeffi C. Giulio Casinovi C. Marini-Bettolo GB. Gazz. Chim. Ital. 1965, 95: 95

<A NAME="RZ11108SS-1C">1c</A> Craveiro AA. Prado AdC. Gottlieb OR. Welerson de Albuquerque PC. Phytochemistry 1970, 9: 1869

<A NAME="RZ11108SS-2">2</A> Araujo CAC. Alefrio LV. Leon LL. Phytochemistry 1998, 49: 751

<A NAME="RZ11108SS-3">3</A> Colobert F. Mazery RD. Solladie G. Carreno MC. Org. Lett. 2002, 4: 1723

<A NAME="RZ11108SS-4A">4a</A> Marumoto S. Jaber JJ. Vitale JP. Rychnovsky SD. Org. Lett. 2002, 4: 3919

<A NAME="RZ11108SS-4B">4b</A> Carreno MC. Mazery RD. Urbano A. Colobert F. Solladie G. J. Org. Chem. 2003, 68: 7779

<A NAME="RZ11108SS-4C">4c</A> Evans PA. Cui J. Gharpure SJ. Org. Lett. 2003, 5: 3883

<A NAME="RZ11108SS-4D">4d</A> Lee E. Kim HJ. Jang WS. Bull. Korean Chem. Soc. 2004, 25: 1609

<A NAME="RZ11108SS-4E">4e</A> Boulad L. BouzzBouz S. Cossy J. Franck X. Figadère B. Tetrahedron Lett. 2004, 45: 6603

<A NAME="RZ11108SS-4F">4f</A> Clarke PA. Martin WHC. Tetrahedron Lett. 2004, 45: 9061

<A NAME="RZ11108SS-4G">4g</A> Chan KP. Loh TP. Org. Lett. 2005, 61: 4491

<A NAME="RZ11108SS-4H">4h</A> Clarke PA. Martin WHC. Tetrahedron 2005, 61: 5433

<A NAME="RZ11108SS-4I">4i</A> Jennings MP. Clemens RT. Tetrahedron Lett. 2005, 46: 2021

<A NAME="RZ11108SS-4J">4j</A> Bohrsch V. Blechert S. Chem. Commun. 2006, 1968

<A NAME="RZ11108SS-4K">4k</A> Lee CHA. Loh TP. Tetrahedron Lett. 2006, 47: 1641

<A NAME="RZ11108SS-4L">4l</A> Prasad KR. Anbarasan P. Tetrahedron 2007, 63: 1089

<A NAME="RZ11108SS-4M">4m</A> Washio T. Yamaguchi R. Abe T. Nambu H. Anada M. Hashimolo S. Tetrahedron 2007, 63: 12037

<A NAME="RZ11108SS-4N">4n</A> Dziedzic M. Furman B. Tetrahedron Lett. 2008, 49: 678

<A NAME="RZ11108SS-5">5</A> Chandrasekhar S. Prakash SJ. Shyamsunder T. Tetrahedron Lett. 2005, 46: 6651

<A NAME="RZ11108SS-6">6</A> Ramnauth J. Poulin O. Rakhit S. Maddaford SP. Org. Lett. 2001, 3: 2013

4-Benzyloxybenzyl triphenylphosphonium bromide was prepared in two steps from commercially available
p-benzyloxybenzyl alcohol using a known protocol, see ref. 4b.