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From Sophorose Lipids to Natural Product Synthesis
Author(s) -
Hoffmann Natalie,
Pietruszka Jörg,
Söffing Christoph
Publication year - 2012
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.201101005
Subject(s) - chemistry , disaccharide , natural product , alcohol , glycoside , stereochemistry , organic chemistry
Sophorose lipids (SL) are a readily available, scalable source for the disaccharide sophorose: In a four‐step sequence the crude product from the fermentation broth was converted to key disaccharide donors 7 that were further utilized in the synthesis of natural products Ebracteatoside C, Zizybeoside I and phenethyl glycoside. While the aglycones for Zizybeoside I and the phenethyl glycoside are commercially available simple primary alcohols, the synthesis of Ebrateatoside C required a secondary allylic alcohol ( R )‐6‐hydroxyoct‐7‐enyl acetate. The enantiomerically pure secondary alcohol was synthesized in two steps using an alcohol dehydrogenase‐catalysed reduction as the key step.