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Total Synthesis Of (±)-Stenine

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. 1990: D. J. Hart ( The Ohio State University ) 1995: P. Wipf ( University Of Pittsburgh )

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Total Synthesis Of (±)-Stenine

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

  2. 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 )

  3. 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

  4. 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)

  5. Retrosynthetic Analysis

  6. 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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