Stereoselective Synthesis of (-)-Cephalotaxine and C- 7 Alkylated - PowerPoint PPT Presentation

Nov 29, 2023 •145 likes •329 views

Stereoselective Synthesis of (-)-Cephalotaxine and C- 7 Alkylated Analogues Loic Plannas, Joelle Perard-Viret and Jacques Royer J. Org. Chem ., 2004 , 69 , 3087. Cephalotaxus drupacea Japanese Plum-Yew Biological Activity Homoharingtonine is

Stereoselective Synthesis of (-)-Cephalotaxine and C- 7 Alkylated Analogues Loic Plannas, Joelle Perard-Viret and Jacques Royer J. Org. Chem ., 2004 , 69 , 3087.
Cephalotaxus drupacea Japanese Plum-Yew
Biological Activity Homoharingtonine is effective against chronic Myelogenous Leukaemia Currently in Phase III clinical trials Isolation Paudler, W. W.; Kerley, G. I.; McKay, J. J. Org. Chem., 1963, 28, 2194 Previous Syntheses Over a dozen racemic syntheses since 1972 Asymmetric Syntheses 1) Mori and Isono, J. Org. Chem ., 1995 , 60 , 115. 2) Nagasaka, Sato and Saeki, Tetrahedron Asymm , 1997 , 8 , 191. 3) Ikeada, et. al, Chem. Pharm Bull ., 1999 , 47 , 983. 4) Tietze and Schirok, J. Am. Chem. Soc ., 1999 , 121 , 10264. 5) Planas, Perard-Viret and Royer, J. Org. Chem ., 2004 , 69 , 3087.
Semmelhack, et. Al., J. Am. Chem. Soc ., 1975 , 97 , 2507
Cephalotaxine can racemize
Mori and Isono, J. Org. Chem ., 1995 , 60 , 115.
Nagasaka, Sato and Saeki, Tetrahedron Asymm , 1997 , 8 , 191. O H H O O O O N N
Ikeada, et. al, Chem. Pharm Bull ., 1999 , 47 , 983.
Tietze and Schirok, J. Am. Chem. Soc ., 1999 , 121 , 10264.
Planas, Perard-Viret and Royer, J. Org. Chem ., 2004 , 69 , 3087.

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