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Unprecedented Cobalt‐Catalyzed Isomerization Reactions to Single Skipped 2,4,7‐Trienes Applied in the Synthesis of Urushiol
Author(s) -
Schmidt Anastasia,
Hilt Gerhard
Publication year - 2014
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201402323
Subject(s) - isomerization , catalysis , chemistry , conjugated system , double bond , cobalt , derivative (finance) , side chain , photochemistry , organic chemistry , polymer , financial economics , economics
The cobalt‐catalyzed isomerization of 1,3‐dienes to 2 Z ,4 E ‐dienes was realized for the very challenging substrates with an additional double bond in the side chain. An isomerization to the conjugated 3,5,7‐triene derivative was not observed, which is in stark contrast to observations with many other isomerization catalysts. Accordingly, the synthesis of the natural product urushiol, which has a sensitive 2 Z ,4 E ,7 Z ‐triene subunit in the side chain, was investigated. The O‐protected urushiol derivative was generated selectively without isomerization to the conjugated 3,5,7‐triene or Z / E ‐isomerization of the double bond at position 7.