Total Synthesis Of (±)-Stenine John D. Ginn and Albert Padwa Org. Lett. 2002, 4(9), Presented by SRINIVASA RAO CHINTALA

Efforts toward the Total Synthesis of Stenine  1990: D. J. Hart ( The Ohio State University )  1995: P. Wipf ( University Of Pittsburgh )  1996: Y. Morimoto ( Osaka City University )  2002: A. Padwa ( Emory University )  2005: J. Aube ( University Of Kansas )  2012: Hongbin Zhang ( Yunnan University )

Albert Padwa  Born in New York City on October3, 1937  BA: Columbia University  PhD: Columbia University with Cheves Walling  NSF Postdoctoral Fellowship with Howard Zimmerman at the University of Wisconsin in 1962–1963  William P. Timmie Professor of Chemistry, Emory University  Published Approximately 820 publications including many reviews and books

Stenine  Isolated in 1992 from the roots of Stemona Species  The roots of Stemonaceae plants are used in traditional Chinese medicines for the treatment of various respiratory ailments  Used for treatment of bronchitis, tuberculosis, pertussis, as well as anti- parasitic agents  Insecticidal activity, active against Bombyx mori (Silk worm Larvae)

Retrosynthetic Analysis

Conclusion 16 steps with the Overall yield of 2.1% All six stereocenters at the azepinoindole core can be derived in high stereoselectivity Described a highly efficient synthesis of (±)-stenine using this IMDAF cycloaddition strategy