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Eight‐Step Synthesis of Routiennocin
Author(s) -
Matsumoto Kenji,
Kozmin Sergey A.
Publication year - 2008
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200700537
Subject(s) - chemistry , polyketide , metathesis , natural product , pyrrole , combinatorial chemistry , ether , total synthesis , ring closing metathesis , stereochemistry , convergent synthesis , salt metathesis reaction , ring (chemistry) , enantioselective synthesis , organic chemistry , biosynthesis , catalysis , polymerization , enzyme , polymer
Routiennocin is a member of a family of polycyclic pyrrole ether antibiotics that simultaneously uncouple oxidative phosphorylation and inhibit ATPase as a result of selective complexation of divalent metal ions. We describe a concise synthesis of routiennocin with the longest linear sequence of 8 steps. Our synthesis features a unique bi‐directional strategy, which entails a sequential ring‐opening/cross metathesis of a highly strained cyclopropenone acetal. This approach enables rapid and highly convergent assembly of the fully extended polyketide subunit of this natural product from readily available homoallylic alcohol precursors.

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