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Synthesis of the Calicheamicin Aryltetrasaccharide Domain Bearing a Reducing Terminus: Coupling of Fully Synthetic Aglycone and Carbohydrate Domains by the Schmidt Reaction
Author(s) -
Halcomb Randall L.,
Boyer Serge H.,
Danishefsky Samuel J.
Publication year - 1992
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199203381
Subject(s) - aglycone , calicheamicin , chemistry , glycosyl , coupling (piping) , combinatorial chemistry , glycosylation , stereochemistry , glycoside , materials science , biochemistry , biology , myeloid leukemia , metallurgy , immunology
The successful coupling of two building blocks constructed by total synthesis is described here as a route to calicheamicin ( 1 ). The aryltetrasaccharide section of 1 is shown for the first time to function as a glycosyl donor for aglycone intermediates.