Concise Total Synthesis of Hydrazidomycin A, a Rare Hydrazide Metabolite of  Streptomyces atratus | Zendy

Meyer Florian | Zendy; Ueberschaar Nico | Zendy; Hertweck Christian | Zendy

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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

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.

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