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Total Synthesis of Glycocinnasperimicin D
Author(s) -
Nishiyama Taihei,
Isobe Minoru,
Ichikawa Yoshiyasu
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200500892
Subject(s) - isocyanate , chemistry , sigmatropic reaction , stereoselectivity , amine gas treating , linkage (software) , total synthesis , stereochemistry , organic chemistry , combinatorial chemistry , catalysis , biochemistry , polyurethane , gene
A three‐fragment coupling strategy afforded the antibiotic glycocinnasperimicin D ( 1 ). The convergent total synthesis features a Heck reaction to form the cinnamoyl glycoside, the [3,3] sigmatropic rearrangement of an allyl cyanate for the stereoselective synthesis of the allyl amine, and the coupling of a glycosyl isocyanate with an amino sugar for the construction of the urea glycoside linkage.