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Review | Regular issue | Vol 85, No. 11, 2012, pp.2617-2649
Published online, 23rd July, 2012
DOI: 10.3987/REV-12-746
Total Synthesis of Manzacidins. An Overview and Perspective

Yasufumi Ohfune,* Kentaro Oe, Kosuke Namba, and Tetsuro Shinada

*Graduate School of Science, Osaka City University, Sugimoto, Sumiyoshi-ku, Osaka 558-8585, Japan

Abstract

Manzacidins belong to a class of non-oroidin bromopyrrole alkaloids and have attracted significant attention from the synthetic community due to not only their expected biological activities but also to their novel structure consisting of a tetrahydropyrimidinecarboxylic acid with an ester-linked bromopyrrole unit. Of particular interest was the stereoselsective construction of the 1,3-diamino groups attached to chiral tertiary and quaternary carbon centers in the tetrahydropyrimidine unit. Since our total synthesis and structure confirmation of manzacidins A and C in 2000, many groups have accessed the enantio- and diastereoselective total syntheses of these alkaloidal amino acids based on novel synthetic methods. This review will focus on recent studies from our laboratory as well as others regarding the total syntheses of manzacidins A, B, C, and D reported to date.