Total Synthesis Of Stenine John D Ginn and

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

Total Synthesis Of (±)-Stenine John D. Ginn and Albert Padwa Org. Lett. 2002, 4(9), 1515 -1517 Presented by SRINIVASA RAO CHINTALA

Efforts toward the Total Synthesis of Stenine v 1990: D. J. Hart ( The

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

Albert Padwa v Born in New York City on October 3, 1937 v BA:

Albert Padwa v Born in New York City on October 3, 1937 v BA: Columbia University v Ph. D: Columbia University with Cheves Walling v NSF Postdoctoral Fellowship with Howard Zimmerman at the University of Wisconsin in 1962– 1963 v William P. Timmie Professor of Chemistry, Emory University v Published Approximately 820 publications including many reviews and books

Stenine v Isolated in 1992 from the roots of Stemona Species v The roots

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

Retrosynthetic Analysis

Retrosynthetic Analysis

Conclusion • 16 steps with the Overall yield of 2. 1% • All six

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

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