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 / L. Banfi, M. Grazia Beretta, L. Colombo, C.M.A. Gennari, C. Scolastico. - In: JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS. - ISSN 0022-4936. - 1982:(1982), pp. 488-490. [10.1039/c39820000488]
Total synthesis of (+)-thermozymocidin (myriocin) from D-fructose
C.M.A. Gennari;C. Scolastico
1982
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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