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Ring Expansions Within the Gold‐Catalyzed Cycloisomerization of O ‐Tethered 1,6‐Enynes. Application to the Synthesis of Natural‐Product‐like Macrocycles
Author(s) -
Simonneau Antoine,
Harrak Youssef,
JeanneJulien Louis,
Lemière Gilles,
MourièsMansuy Virginie,
Goddard JeanPhilippe,
Malacria Max,
Fensterbank Louis
Publication year - 2013
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201200484
Subject(s) - cycloisomerization , ring (chemistry) , cationic polymerization , catalysis , product (mathematics) , chemistry , natural product , combinatorial chemistry , computer science , stereochemistry , organic chemistry , mathematics , geometry
Goldenyne: O ‐tethered 1,6‐enynes that contain a strained ring at the 3 position can cycloisomerize upon cationic gold(I) catalysis through a ring‐expansion process. A two‐step sequence allows the transformation of the cyclized compounds into ketomacrolactones, which are reminiscent of natural products.