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Pure Appl. Chem. 76(11), 1967-1983, 2004

Pure and Applied Chemistry

Vol. 76, Issue 11

Domino reactions in the synthesis of heterocyclic natural products and analogs

L. F. Tietze and N. Rackelmann

Institut für Organische und Biomolekulare Chemie, Georg-August Universität- Göttingen, 37077 Göttingen, Germany

Abstract: 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.

* Plenary lecture presented at the 5th Florida Heterocyclic Conference, Gainesville, FL, USA, 7-10 March 2004. Other presentations are published in this issue, pp. 1933-1983.

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