δ‐Peptide Analogues of Pyranosyl‐RNA,Part 1
, Nucleo‐δ‐peptides Derived from Conformationally Constrained Nucleo‐δ‐amino Acids: Preparation of Monomers |
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Authors: | Gunter Karig,Andreas Fuchs,Arne Bü sing,Tilmann Brandstetter,Stefan Scherer,Jan W. Bats,Albert Eschenmoser,Gerhard Quinkert |
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Abstract: | Cyclic nucleo‐δ‐amino acids that constitute monomers of a conformationally constrained nucleo‐δ‐peptide base‐pairing system have been prepared. Their synthesis starts with an enantioselectively catalyzed chirogenic Diels‐Alder reaction, proceeds via a regioselective ε‐iodolactamization process, and ends with a regio‐ as well as diastereoselective introduction of nucleobases through SN2‐type opening of a transiently formed N‐acylaziridine ring. Extensive use of X‐ray crystal‐structure analysis has been made to support structure assignments. |
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