%A JD Moretti
%A X Wang
%A DP Curran
%J Journal of the American Chemical Society
%T Minimal fluorous tagging strategy that enables the synthesis of the complete stereoisomer library of SCH725674 macrolactones
%X Four mixtures of four fluorous-tagged quasiisomers have been synthesized, demixed, and detagged to make all 16 stereoisomers of the macrocyclic lactone natural product Sch725674. A new bare-minimum tagging pattern needs only two tags-one fluorous and one nonfluorous-to encode four isomers. The structure of Sch725674 is assigned as (5R,6S,8R,14R,E)-5,6,8-trihydroxy-14- pentyloxacyclotetradec-3-en-2-one. Various comparisons of spectra of 32 lactones (16 with tags, 16 without) and 16 ester precursors (8 with tags, 8 without) provide insights into when and why related compounds have the same or different spectra. ? 2012 American Chemical Society.
%N 18
%P 7963 - 7970
%V 134
%D 2012
%R 10.1021/ja302260d
%L pittir17941