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. Author manuscript; available in PMC: 2018 Nov 1.
Published in final edited form as: J Am Chem Soc. 2017 Oct 20;139(43):15460–15466. doi: 10.1021/jacs.7b08775

Figure 3.

Figure 3

Reaction conditions for diastereoselective conjugate addition of boronic acids to thiostrepton. a. Model reaction used to develop a diastereoselective process. b. Outcome of the model reaction conducted under varied reaction conditions. c. HPLC traces of crude reactions conducted under aqueous conditions (described in Fig. 2) and methanolic conditions (Fig. 3b, entry 9). d. Outcome of diastereoselective reactions using varied boronic acid substrates. Reactions were conducted under conditions shown in Fig. 3b, entry 9. UPLC traces of crude reactions are shown to exemplify the change in diastereoselectivity in the presence of each ligand. Conversions are based on integration of the UPLC traces using uncorrected areas. Stereochemistry is depicted based on analogy to the stereochemical outcome of reactions of Dha monomers conducted under comparable conditions (vide infra).