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Synergistic Gold and Copper Dual Catalysis for Intramolecular Glaser–Hay Coupling: Rapid Total Synthesis of Ivorenolide B
Author(s) -
Rangaraju Sudheer K.,
Gonela Uma Maheshwar,
Kavita Aala,
Yadav Jhillu S.,
Mohapatra Debendra K.
Publication year - 2018
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.201800708
Subject(s) - chemistry , intramolecular force , catalysis , conjugated system , copper , combinatorial chemistry , selectivity , stereochemistry , organic chemistry , polymer
A synergistic dual catalysis approach involving gold and copper catalysts for the synthesis of macrolactones bearing 1,3‐butadiynes through an intramolecular Glaser–Hay coupling reaction in good yield is described. This dual catalytic system exhibited good selectivity, reactivity and functional group tolerance. This unique process offers a paradigm shift: the potential as well as the versatility of this novel method is not only exemplified for the synthesis of macrolactones of different ring size but also for the rapid total synthesis of ivorenolide B, a new class of macrolides endowed with conjugated 1,3‐diyne motif, having impressive immunosuppressive activities.