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).
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/175906
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