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Synthesis of the Bioherbicidal Fungus Metabolite Macrocidin A

Author:
Haase, Robert G., Schobert, Rainer
Source:
Organic letters 2016 v.18 no.24 pp. 6352-6355
ISSN:
1523-7052
Subject:
acylation, bromides, epoxides, fungi, metabolites, moieties, tyrosine
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.
Agid:
5792215