Synthesis of the Bioherbicidal Fungus Metabolite Macrocidin A
Robert G Haase1, Rainer Schobert1
1Organic Chemistry Laboratory, University of Bayreuth , Universitätsstrasse 30, 95440 Bayreuth, Germany.
Abstract:
The second total synthesis of macrocidin A afforded the bioherbicidal fungal metabolite in 16 steps starting from doubly protected l-tyrosine. The 3-octanoyl side chain with the α-methyl group and an ω-bromo epoxide already in place was attached to the tetramic acid via a Yoshii-Yoda acylation, and the macrocycle was eventually closed in 55% yield by a Williamson etherification between the phenolate and the epoxy bromide.
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