TY - JOUR
T1 - Effects of temperature and concentration in some ring closing metathesis reactions
AU - Yamamoto, Kana
AU - Biswas, Kaustav
AU - Gaul, Christoph
AU - Danishefsky, Samuel J.
N1 - Funding Information:
Support for this research was provided by the National Institutes of Health (CA 28824). Postdoctoral Fellowship support is gratefully acknowledged by K.Y. (The Helen Hay Whitney Foundation), K.B. (US Army Breast Cancer Research Program, DAMD-17-98-1-8155), and C.G. (Deutscher Akademischer Austauschdienst, DAAD). Dr. George Sukenick (NMR Core Facility, Sloan-Kettering Institute) is acknowledged for NMR and mass spectral analyses. We also thank Dr. Alex Rivkin for his assistance in preparing compound 14 .
Copyright:
Copyright 2017 Elsevier B.V., All rights reserved.
PY - 2003/4/14
Y1 - 2003/4/14
N2 - Ring closing metathesis (RCM) has emerged as a powerful tool to construct macrocyclic ring systems. However, the product distribution of monomer and oligomers is often a problem in the formation of medium to large rings. In the course of synthetic studies on the natural product radicicol and its analogs, we have found that the reaction temperature, along with concentration, has significant impact on the outcome of the product ratio. Specifically, carrying out the RCM reaction in refluxing toluene (110°C) at higher dilution affords improved yields of the monomeric macrocycle. Similar observations for another family of macrolactone natural products, the epothilones, are also reported.
AB - Ring closing metathesis (RCM) has emerged as a powerful tool to construct macrocyclic ring systems. However, the product distribution of monomer and oligomers is often a problem in the formation of medium to large rings. In the course of synthetic studies on the natural product radicicol and its analogs, we have found that the reaction temperature, along with concentration, has significant impact on the outcome of the product ratio. Specifically, carrying out the RCM reaction in refluxing toluene (110°C) at higher dilution affords improved yields of the monomeric macrocycle. Similar observations for another family of macrolactone natural products, the epothilones, are also reported.
KW - Epothilone
KW - Product distribution
KW - RCM
KW - Radicicol
KW - Ring closing metathesis
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U2 - 10.1016/S0040-4039(03)00618-X
DO - 10.1016/S0040-4039(03)00618-X
M3 - Article
AN - SCOPUS:0037436934
VL - 44
SP - 3297
EP - 3299
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 16
ER -