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Expedient Synthesis of Large‐Ring trans ‐Enamide Macrolides by CuI‐Mediated Intramolecular Coupling of Vinyl Iodide with Amide: Total Synthesis of Palmyrolide A
Author(s) -
Yadav Jhillu Singh,
Suresh Borra,
Srihari Pabbaraja
Publication year - 2016
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.201600325
Subject(s) - chemistry , intramolecular force , iodide , amide , ring (chemistry) , total synthesis , stereochemistry , natural product , combinatorial chemistry , ligand (biochemistry) , halide , organic chemistry , receptor , biochemistry
An efficient and improved procedure for copper‐catalyzed coupling of vinyl iodide with amide in an intramolecular fashion is described. The protocol utilizes a combination of copper iodide, CsF and (±)‐1,2‐diaminocyclohexane as ligand. The vinyl iodide couples efficiently with the amide to generate an enamide macrolide without any alteration in the double ‐bond geometry. The developed method was applied in the synthesis of several large‐ring enamide macrolides, and for the total synthesis of natural product palmyrolide A and homologated sanctolide A.