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Stereocontrolled Synthesis of an Epimer of the C(19)‐to‐C(27) Segment of Rifamycin S
Author(s) -
Tschamber Théophile,
WaespeS̆arčevic̀ Nada,
Tamm Christoph
Publication year - 1986
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.19860690311
Subject(s) - chemistry , epimer , aldol reaction , moiety , stereochemistry , propionate , rifamycin , organic chemistry , antibiotics , biochemistry , catalysis
The synthesis of the ansa chain of rifamycin S ( 1 ), corresponding to the C(19) to C(27) moiety, epimeric at C(23), is described starting from dimethyl xylo ‐3‐hydroxy‐2,4‐dimethylglutarate ( 4 ). The diester 4 was transformed to the C 10 ‐diester 16 by two threo ‐aldol condensations with 2,6‐dimethylphenyl propionate ( 5 ).
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