Practical stereoselective synthesis of eribulin fragment toward building a hybrid macrocyclic toolbox
Ravikumar Jimmidi1, Shiva Krishna Reddy Guduru, Prabhat Arya
1Dr. Reddy's Institute of Life Sciences (DRILS) , University of Hyderabad Campus, Hyderabad 500046, India.
Abstract:
A practical stereoselective synthesis to obtain the substituted furan ring as the substructure of eribulin is developed. An asymmetric syn-aldol and intramolecular oxy-Michael were two key steps in our approach. The functionalized furan derivatives were then utilized further to build the 14- and 12-membered macrocyclic diversity as trans- and cis-fused (C-29 and C-30) compounds. This is the first report of building a chemical toolbox with macrocyclic small molecules having trans- or cis-fused 14- or 12-membered rings containing the substructure of eribulin and its diastereomer.
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