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 )

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