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Concise Total Synthesis of Hydrazidomycin A, a Rare Hydrazide Metabolite of Streptomyces atratus
Author(s) -
Meyer Florian,
Ueberschaar Nico,
Hertweck Christian
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300532
Subject(s) - chemistry , hydrazide , hydrazine (antidepressant) , streptomyces , alkyne , total synthesis , yield (engineering) , metabolite , phthalimide , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , biochemistry , materials science , genetics , biology , bacteria , metallurgy
Abstract Hydrazidomycins A–C and elaiomycins B–C represent a family of unusual, naturally occurring enehydrazides produced by Streptomyces sp. A general synthetic approach to access these densely functionalized hydrazine derivatives is exemplified by the first total synthesis of hydrazidomycin A. The modular synthesis involves a ruthenium‐catalyzed hydroamidation of an alkyne and a hydrazide‐derived phthalimide to yield predominantly the Z ‐configured enehydrazide.