caa a22 4500 378944010 CHVBK 20180305123659.0 cr unu---uuuuu 161128e20040101xx s 000 0 eng 10.1351/pac200476111967 doi (NATIONALLICENCE)gruyter-10.1351/pac200476111967 Domino reactions in the synthesis of heterocyclic natural products and analogs [Elektronische Daten] [L. F. Tietze, N. Rackelmann] Domino reactions are defined as processes of two or more bond-forming reactions under identical conditions, in which the subsequent transformation takes place at the functionalities obtained in the former transformation. They allow the efficient synthesis of complex molecules from simple substrates in an ecologically and economically favorable way. A very powerful domino process is the domino Knoevenagel-hetero-Diels-Alder reaction, in which an aldehyde or an beta-ketoester is condensed with a 1,3-dicarbonyl compound or a heteroanalog to give a 1-oxa-1,3-butadiene, which can undergo an inter- or intramolecular hetero-Diels-Alder reaction with dienophiles such as enol ethers or alkenes. The products are dihydropyrans, which can be transformed in a variety of ways. Thus, an extension of the process is the synthesis of highly substituted pyrrolidines, piperidines, and azepanes using aminoaldehydes. The process has also been employed for the enantioselective total synthesis of a variety of alkaloids, such as indol- and ipecacuanha alkaloids. In another domino process, erythrina and homoerythrina alkaloids have been prepared from simple phenylethylamines and ketoesters. © 2013 Walter de Gruyter GmbH, Berlin/Boston Tietze L. F. Institut für Organische und Biomolekulare Chemie, Georg-August Universität- Göttingen, 37077 Göttingen, Germany aut Rackelmann N. Institut für Organische und Biomolekulare Chemie, Georg-August Universität- Göttingen, 37077 Göttingen, Germany aut Pure and Applied Chemistry De Gruyter 76/11(2004-01-01), 1967-1983 0033-4545 76:11<1967 2004 76 pac https://doi.org/10.1351/pac200476111967 text/html Onlinezugriff via DOI 1 research article jats NATIONALLICENCE 856 40 https://doi.org/10.1351/pac200476111967 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Tietze L. F. Institut für Organische und Biomolekulare Chemie, Georg-August Universität- Göttingen, 37077 Göttingen, Germany aut NATIONALLICENCE 700 1- Rackelmann N. Institut für Organische und Biomolekulare Chemie, Georg-August Universität- Göttingen, 37077 Göttingen, Germany aut NATIONALLICENCE 773 0- Pure and Applied Chemistry De Gruyter 76/11(2004-01-01), 1967-1983 0033-4545 76:11<1967 2004 76 pac CC0 http://creativecommons.org/publicdomain/zero/1.0 nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-gruyter