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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.
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Nishiyama et al. (2005) studied this question.
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