Stereoselective Synthesis of (−)-Pinidinone
Gundeti Shankaraiah
Division of Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Uppal Road, Hyderabad 500607, India
Search for more papers by this authorTiruvayamudi Vijaya Kumar
Division of Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Uppal Road, Hyderabad 500607, India
Search for more papers by this authorGuvvala Venkateswara Reddy
Division of Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Uppal Road, Hyderabad 500607, India
Search for more papers by this authorJanaswamy Madhusudana Rao
Division of Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Uppal Road, Hyderabad 500607, India
Search for more papers by this authorCorresponding Author
Katragadda Suresh Babu
Division of Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Uppal Road, Hyderabad 500607, India
Division of Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Uppal Road, Hyderabad 500607, IndiaSearch for more papers by this authorGundeti Shankaraiah
Division of Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Uppal Road, Hyderabad 500607, India
Search for more papers by this authorTiruvayamudi Vijaya Kumar
Division of Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Uppal Road, Hyderabad 500607, India
Search for more papers by this authorGuvvala Venkateswara Reddy
Division of Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Uppal Road, Hyderabad 500607, India
Search for more papers by this authorJanaswamy Madhusudana Rao
Division of Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Uppal Road, Hyderabad 500607, India
Search for more papers by this authorCorresponding Author
Katragadda Suresh Babu
Division of Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Uppal Road, Hyderabad 500607, India
Division of Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Uppal Road, Hyderabad 500607, IndiaSearch for more papers by this authorAbstract
A simple and efficient stereoselective linear approach to the total synthesis of (−)-pinidinone has been accomplished starting from propane-1,3-diol, and employing Maruoka asymmetric allylation and Grubbs' olefin cross-metathesis as the key steps.
References
- 1 P. D. Bailey, P. A. Millwood, P. D. Smith, Chem. Commun. 1998, 633.
- 2 M. Schneider, in ‘Alkaloids: Chemical and Biological Perspectives’, Ed. S. W. Pelletier, Pergamon, Oxford, 1996, Vol. 10, pp. 155–299.
- 3 J. N. Tawara, A. Blokhin, T. A. Foderaro, F. R. Stermitz, H. Hope, J. Org. Chem. 1993, 58, 4813.
- 4a K. Csatayova, I. Spanik, V. Durisova, P. Szolcsanyi, Tetrahedron Lett. 2010, 51, 6611;
- 4b S. Freville, P. Delbecq, V. M. Thuy, H. Petit, J.-P. Celerier, G. Lhommet, Tetrahedron Lett. 2001, 42, 4609;
- 4c M. Kavala, F. Mathia, J. Kozissek, P. Szolcsanyi, J. Nat. Prod. 2011, 74, 803;
- 4d M. J. Munchhof, A. I. Mayers, J. Am. Chem. Soc. 1995, 117, 5399.
- 5 C. L. J. Wang, M. A. Wuonola, Org. Prep. Proced. Int. 1992, 24, 583; S. Laschat, T. Dickner, Synthesis 2000, 1781.
- 6
R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413;
S. K. Armstrong, J. Chem. Soc., Perkin Trans. 1 1998, 371;
M. E. Maier, Angew. Chem., Int. Ed. 2000, 39, 2073;
10.1002/1521-3773(20000616)39:12<2073::AID-ANIE2073>3.0.CO;2-0 CAS PubMed Web of Science® Google ScholarL. Yet, Chem. Rev. 2000, 100, 2963; A. Fürstner, Angew. Chem., Int. Ed. 2000, 39, 3012;10.1002/1521-3773(20000901)39:17<3012::AID-ANIE3012>3.0.CO;2-G CAS PubMed Web of Science® Google ScholarT. M. Trnka R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18; S. J. Connon, S. Blechert, Angew. Chem., Int. Ed. 2003, 42, 1900.
- 7 P. Schwab, M. B. France, J. W. Ziller, R. H. Grubbs, Angew. Chem., Int. Ed. Engl. 1995, 34, 2039; P. Schwab, R. H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 100.
- 8 M. Scholl, S. Ding, C. W. Lee, R. H. Grubbs, Org. Lett. 1999, 1, 953.
- 9 A. H. Hoveyda, D. G. Gillingham, J. J. Van Veldhuizen, O. Kataoka, S. B. Garber, J. S. Kingsbury, J. P. A. Harrity, Org. Biomol. Chem. 2004, 2, 8.
- 10a R. S. C. Kumar, E. Sreedhar, G. V. Reddy, K. S. Babu, J. M. Rao, Tetrahedron: Asymmetry 2009, 20, 1160;
- 10b E. Sreedhar, R. S. C. Kumar, G. V. Reddy, A. Robinson, K. S. Babu, J. M. Rao, Tetrahedron: Asymmetry 2009, 20, 440;
- 10c G. V. Reddy, R. S. C. Kumar, K. S. Babu, J. M. Rao, Tetrahedron Lett. 2009, 50, 4117;
- 10d R. S. C. Kumar, G. V. Reddy, G. Shankaraiah, K. S. Babu, J. M. Rao, Tetrahedron Lett. 2010, 51, 1114;
- 10e G. V. Reddy, R. S. C. Kumar, E. Sreedhar, K. S. Babu, J. M. Rao, Tetrahedron Lett. 2010, 51, 1723.
- 11a S. Nanda, J. S. Yadav, Tetrahedron: Asymmetry 2003, 14, 1799;
- 11b B. Das, S. Nagendra, C. R. Reddy, Tetrahedron: Asymmetry 2010, 22, 1249.
- 12 M. Frigerio, M. Santagostino, Tetrahedron Lett. 1994, 35, 8019.
- 13a H. Hanawa, T. Hashimoto, K. Maruoka, J. Am. Chem. Soc. 2003, 125, 1708;
- 13b D. K. Mohapatra, P. Karthik, J. S. Yadav, Helv. Chim. Acta 2012, 95, 1226.
- 14 C. A. I. Capaccio, O. Varela, Tetrahedron: Asymmetry 2000, 11, 4945.
- 15 I. Paterson, M. Tudge, Tetrahedron 2003, 59, 6833.
- 16 D. B. Dess, J. C. Martin, J. Am. Chem. Soc. 1991, 113, 7277.
- 17 S. Randl, S. Blechert, J. Org. Chem. 2003, 68, 8879.
- 18 T. Esumi, M. Zhao, T. Kawakani, M. Fukumoto, Tetrahedron Lett. 2008, 49, 2692.
- 19 S. BouzBouz, R. Simmons, J. Cossy, Org. Lett. 2004, 6, 3465, and refs. cit. therein.
- 20 S. Randl, S. Blechert, Tetrahedron Lett. 2004, 45, 1167.
