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Efficient, Enantioselective Organocatalytic Synthesis of Trichostatin A
Author(s) -
Zhang Shilei,
Duan Wenhu,
Wang Wei
Publication year - 2006
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200606106
Subject(s) - enantioselective synthesis , chemistry , racemization , aldol reaction , trichostatin a , yield (engineering) , ketone , total synthesis , organocatalysis , combinatorial chemistry , organic chemistry , stereochemistry , catalysis , histone deacetylase , biochemistry , materials science , metallurgy , gene , histone
An efficient, highly stereocontrolled total synthesis of trichostatin A ( 1 ) has been achieved in 9 steps with 17.4 % overall yield and >99 % optical purity from readily available achiral starting materials. The key features of this synthesis include the L ‐proline‐promoted, highly enantioselective cross‐aldol reaction as a crucial step for the construction of the C‐6 chiral center and the minimization of racemization by final step oxidation of the OH group to a ketone at position 7.