1,721,253 research outputs found

    Asymmetrized Tris(hydroxymethyl)methane and Related Synthons: Enantioselective Preparation and Synthetic Applications

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    Asymmetrized tris(hydroxymethyl)methane (THYM*) is a new chiral building block easily accessible in both enantiomeric forms by a chemoenzymatic methodology. The presence of three synthetically equivalent masked hydroxymethyl groups and a high degree of latent symmetry (C3v) makes this synthon very versatile in synthetic applications. This review describes its preparation and a series of elaborations (with particular enphasis on the diastereoselective generation of additional chiral centers) leading to advanced intermediated for the preparation of biologically active compounds

    Synthesis of N-Fused “Lactendiynes”

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    New “lactendiynes”, characterized by the fusion at C-4 and N-1 of a β-lactam with a hydroxylated 10-membered cyclic enediyne, were synthesized. Studies on their reactivity have shown that this type of fusion with the azetidinone represents a sufficient “safety-catch” against cycloaromatization. These compounds are relatively reactive toward basic hydrolysis, affording monocyclic enediynes which undergo fast cycloaromatization at room temperature
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