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Asymmetric Synthesis of 1-Aza-4-deoxypicropodophyllotoxin.

Authors :
Aigret, Benoit M.
Jacobs, Jeroen
Van Meervelt, Luc
De Borggraeve, Wim M.
Source :
Synlett; 6/1/2013, Vol. 24 Issue 9, p1097-1100, 4p
Publication Year :
2013

Abstract

In our search for new easily accessible analogues based on the natural product podophyllotoxin, we synthesized 1-aza-4-deoxypicropodophyllotoxin in good overall yield and excellent enantioselectivity. The synthesis was centered around a direct asymmetric Mannich reaction using D-proline as the key step for introduction of the chiral centres. Our synthesis of 1-aza-4-deoxypodophyllotoxin was hindered through the increased instability towards epimerization of the C2 position. We did, however, synthesized a new scaffold based on the opened lactone analogue. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
09365214
Volume :
24
Issue :
9
Database :
Complementary Index
Journal :
Synlett
Publication Type :
Academic Journal
Accession number :
87741436
Full Text :
https://doi.org/10.1055/s-0033-1338414