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Stereoselective Total Synthesis of Tubulysin V
Author(s) -
Wang Rui,
Tian Ping,
Lin Guoqiang
Publication year - 2013
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201200984
Subject(s) - chemistry , allylic rearrangement , amine gas treating , imine , stereoselectivity , bromide , yield (engineering) , aqueous solution , total synthesis , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis , materials science , metallurgy
The total synthesis of tubulysin V was accomplished in 1.0% overall yield with linear 13 steps. Our synthetic strategy featured the following two reactions. One is zinc‐mediated aza‐Barbier reaction of ( R )‐ N ‐ tert ‐butanesulfinyl imine 8 with β ‐ester group functionalized allylic bromide 9 to afford the chiral homo‐allylic amine ( 7 ); the other is to employ the methodology of aqueous indium‐mediated aza‐Barbier reaction previously developed by our group, giving the chiral homo‐allylic amine 13 with high efficiency.