Comparison of solution-phase and solid-phase syntheses of a restrained proline-containing analogue of the nodularin macrocycle

Article abstract of DOI:10.1016/S0040-4039(97)01253-7

The solution-phase synthesis of a restrained (2S)-proline-containing analogue of the nodularin macrocycle, cyclo-[β-Ala-(2R)-Glu(α-OMe)-γ-(2S)-Pro-(2R)-Asp(α-OMe)-β-(2S)-Phe-], is described and compared to two solid-phase syntheses of the same cyclic isopentapeptide diester; one in which Fmoc-(2S)-Phe-β-Ala-(2R)-Glu(α-OMe)-γ-(2S)-Pro-(2R)-Asp(α-O-Wang Resin)-β-OAllyl is deprotected and then cyclised on the resin and one in which this same precursor is removed from the resin prior to cyclisation.