title: Practical stereoselective synthesis of eribulin fragment toward building a hybrid macrocyclic toolbox.
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.
authors.affiliation: Dr. Reddy's Institute of Life Sciences (DRILS) , University of Hyderabad Campus, Hyderabad 500046, India.
authors.forename: Ravikumar
authors.initials: R
authors.lastname: Jimmidi
authors.forename: Shiva Krishna Reddy
authors.initials: SK
authors.lastname: Guduru
authors.forename: Prabhat
authors.initials: P
authors.lastname: Arya
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D000095662:Polyether Polyketides
chemical_list: D000447:Aldehydes; D005663:Furans; D007659:Ketones; D047028:Macrocyclic Compounds; C116609:3-hydroxybutanal; C490954:eribulin; D000095662:Polyether Polyketides