A total synthesis of thermozymocidin (1) has been achieved using D-fructose as the chiral synthon; the key steps of the synthesis are the transformation of D-fructose into 2-amino-2-deoxy-2-hydroxymethyl-D-mannonic acid (4) and the stereoselective synthesis of the disubstituted (E)-double bond by reaction of the (E)-alkenylcuprate (17) with the tosylate (14).
Total Synthesis of (+) Thermozymocidin (Myriocin) from D-Fructose
BANFI, LUCA;
1982-01-01
Abstract
A total synthesis of thermozymocidin (1) has been achieved using D-fructose as the chiral synthon; the key steps of the synthesis are the transformation of D-fructose into 2-amino-2-deoxy-2-hydroxymethyl-D-mannonic acid (4) and the stereoselective synthesis of the disubstituted (E)-double bond by reaction of the (E)-alkenylcuprate (17) with the tosylate (14).
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