Thiede, Sebastian; Wosniok, Paul R.; Herkommer, Daniel; Debnar, Thomas; Tian, Maoqun; Wang, Tongtong; Schrempp, Michael; Menche, Dirk published an article in 2017, the title of the article was Total Synthesis of Leupyrrins A1 and B1, Highly Potent Antifungal Agents from the Myxobacterium Sorangium cellulosum.Name: tert-Butyl trichloroacetimidate And the article contains the following content:
Full details on the design, elaboration, and application of efficient strategies for the high-yielding total syntheses of leupyrrins A1 and B1 (I and II, resp.), unique antifungal agents from the myxobacterium Sorangium cellulosum, are reported. A sequential zirconocene-mediated diyne-cyclization, and regioselective opening of the zirconacyclopentadiene intermediate enabled a concise entry into the unique dihydrofuran fragment, whereas another domino reaction was developed for the butyrolactone involving a one-pot lactol opening, stereoselective aldehyde addition and in situ lactonization. Furthermore, an innovative sp2-sp3-cross-coupling for pyrrole functionalization and an optimized HATU-mediated amide coupling protocol of two elaborate fragments were established. In addition, an unusual protective group strategy, involving a Teoc-acetonide protected amine in combination with tert-Bu and acetate esters, was successfully elaborated. These tactics and strategies are generally useful and may be also applied in the synthesis of other functionalized compounds It is expected that the material which was obtained by these total syntheses will enable the further exploration of the biol. profile of these potent antifungal agents. The experimental process involved the reaction of tert-Butyl trichloroacetimidate(cas: 98946-18-0).Name: tert-Butyl trichloroacetimidate
The Article related to leupyrrin a1 b1 synthesis, zirconocene mediated diyne cyclization regioselective opening zirconacyclopentadiene leupyrrin synthesis, lactol ring opening stereoselective aldehyde addition lactonization leupyrrin synthesis, cross coupling pyrrole functionalization leupyrrin synthesis, hatu mediated amide coupling leupyrrin synthesis and other aspects.Name: tert-Butyl trichloroacetimidate
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