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Totalsynthese des Antibioticums Anisomycin
Author(s) -
Felner I.,
Schenker K.
Publication year - 1970
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19700530409
Subject(s) - anisomycin , chemistry , decarboxylation , pictet–spengler reaction , stereochemistry , derivative (finance) , cleavage (geology) , total synthesis , organic chemistry , catalysis , biochemistry , protein biosynthesis , geotechnical engineering , fracture (geology) , financial economics , engineering , economics
The synthesis of the antibiotic anisomycin ( 1 ) is described. In the key step 3, 4‐dimethoxy‐thiopyrrolidone ( 16 ), prepared from diethyl L ‐( + )‐tartarate ( 4 ) was converted to the thioiminoester 18 , which upon treatment with trimethylphosphite yielded the benzylidene derivative 19 . Cleavage of the ester group of 19 and hydrogenation of the decarboxylation product gave the two isomers 21 and 22 . 22 was converted into desacetylanisomycin ( 3 ) and anisomycin ( 1 ).
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