Synthesis of cyclic peptidomimetics from aldol building blocks |
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Authors: | Sasmal Sanjita Geyer Armin Maier Martin E |
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Affiliation: | Institut für Organische Chemie, Universit?t Tübingen, Auf der Morgenstelle 18, D-72076 Tübingen, Germany. |
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Abstract: | Aldol products (3-hydroxy acids) with an allyl-protected hydroxy group were converted to amino alcohols by Curtius rearrangement. Combination of the carboxylic acid with the amino alcohols gave the amides 10. Ring-closing metathesis led to the 12-membered lactams 12 as mixtures of E/Z-isomers. The scheme was also transferred to the solid-phase. In this case the macrolactams are formed via cyclorelease. For a pair of E/Z-isomers the solution conformation was determined by ROESY spectroscopy. |
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