title: Total synthesis of dolabelide C: a phosphate-mediated approach.
abstract: The first synthesis of dolabelide C (1), a cytotoxic marine macrolide, is reported utilizing a phosphate tether-mediated approach. Bicyclic phosphates (S,S,S(P))-5 and (R,R,R(P))-5 serve as the central building blocks for the construction of two major 1,3-anti-diol subunits in 1 through selective cleavage pathways, regioselective olefin reduction, and cross-metathesis. Overall, phosphate-mediated processes provided copious amounts of both major subunits allowing for a detailed RCM macrocyclization study to the 24-membered macrolactone 1.
authors.affiliation: Department of Chemistry, University of Kansas, Lawrence, Kansas 66045, United States. phanson@ku.edu
authors.forename: Paul R
authors.initials: PR
authors.lastname: Hanson
authors.forename: Rambabu
authors.initials: R
authors.lastname: Chegondi
authors.forename: John
authors.initials: J
authors.lastname: Nguyen
authors.forename: Christopher D
authors.initials: CD
authors.lastname: Thomas
authors.forename: Joshua D
authors.initials: JD
authors.lastname: Waetzig
authors.forename: Alan
authors.initials: A
authors.lastname: Whitehead
mesh_terms: D002384:Catalysis; D003500:Cyclization; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry*; D010710:Phosphates / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D018942:Macrolides; D010710:Phosphates; C524147:dolabelide C