Synthesis, Table of Contents PAPER © Georg Thieme Verlag Stuttgart ˙ New York Total Synthesis of (+)-Dodoneine and Its 6-Epimer Gowravaram Sabitha*, Vangala Bhaskar, S. Siva Sankara Reddy, Jhillu S. YadavOrganic Division I, Indian Institute of Chemical Technology, Hyderabad 500007, IndiaFax: +91(40)27160512; e-Mail: gowravaramsr@yahoo.com; Recommend Article Abstract Buy Article All articles of this category Abstract The total synthesis of dodoneine and its 6-epimer is described, using HKR of epoxide and reduction with SmI2 reactions as key steps, respectively. Key words dodoneine - epidodoneine - trimethylsulfonium iodide - HKR - SmI2 - RCM Full Text References References 1 Ouedragogo M. Carreyre H. Vandebrouck C. Bescond J. Raymond G. Guissou I.-P. Cognard C. Becq F. Potreau D. Cousson A. Marrot J. Coustard J.-M. J. Nat. Prod. 2007, 70: 2006 2a Robert R. Thoreau V. Norez C. Cantereau A. Mettey Y. Rogier C. Becq F. J. Biol. Chem. 2004, 279: 21160 2b Vandebrouck C. Melin P. Norez C. Robert R. Guibert C. Mettey Y. Becq F. Respir. Res. 2006, 7: 113 3a Bercedo PA. Falomir E. Murga J. Carda M. Marco JA. Eur. J. Org. Chem. 2008, 4015 3b Srihari P. Rajendar G. Rao RS. Yadav JS. Tetrahedron Lett. 2008, 49: 5590 3c Dittoo A. Bellosta V. Cooy J. Synlett 2008, 2459 4a Sabitha G. Sudhakar K. Reddy NM. Rajkumar M. Yadav JS. Tetrahedron Lett. 2005, 46: 6567 4b Sabitha G. Narjis F. Swapna R. Yadav JS. Synthesis 2006, 2879 4c Sabitha G. Reddy EV. Yadagiri K. Yadav JS. Synthesis 2006, 3270 4d Sabitha G. Sudhakar K. Yadav JS. Tetrahedron Lett. 2006, 47: 8599 4e Sabitha G. Bhaskar V. Yadav JS. Tetrahedron Lett. 2006, 47: 8179 4f Sabitha G. Swapna R. Reddy EV. Yadav JS. Synthesis 2006, 4242 4g Sabitha G. Bhikshapathi M. Yadav JS. Synth. Commun. 2007, 37: 561 4h Sabitha G. Gopal P. Yadav JS. Synth. Commun. 2007, 37: 1495 4i Sabitha G. Yadagiri K. Yadav JS. Tetrahedron Lett. 2007, 48: 1651 4j Sabitha G. Gopal P. Reddy CN. Yadav JS. Tetrahedron: Asymmetry 2009, 20: 184 5 Lescure P. Huet F. Synthesis 1987, 404 6a Schaus SE. Brandes BD. Larrow JF. Tokunaga M. Hansen KB. Gould AE. Furrow ME. Jacobsen EN. J. Am. Chem. Soc. 2002, 124: 1307 6b Louis JT. Nelson WL. J. Org. Chem. 1987, 52: 1309 7 Rychnovsky SD. Rogers BN. Richardson RI. Acc. Chem. Res. 1998, 31: 9 8a Fürstner A. Angew. Chem. Int. Ed. 2000, 39: 3012 8b Tanaka TM. Grubbs RH. Acc. Chem. Res. 2001, 34: 18 8c Grubbs RH. Tetrahedron 2004, 44: 2449 8d Grubbs RH. Tetrahedron 2004, 60: 7117 8e Love JA. In Handbook of Metathesis Vol. 2: Grubbs RH. Wiley-VCH; Weinheim: 2003. p.296-322 9 Evans DA. Gauchet-Prunet JA. J. Org. Chem. 1993, 58: 2446 10a Petrier C. Luche JL. J. Org. Chem. 1985, 50: 910 10b Einhorn C. Luche JL. J. Organomet. Chem. 1987, 322: 177 10c Chattopadhyay A. J. Org. Chem. 1996, 61: 6104 11 Dess PB. Martin JC. J. Am. Chem. Soc. 1978, 100: 300 12a Keck GE. Wager CA. Org. Lett. 2000, 2: 2307 12b Keck GE. Wager CA. Sell T. Wager T. S. J. Org. Chem. 1999, 64: 2172
