Abstract
Compounds with a 1,2-, 1,4- and 1,6-dioxygen pattern and related bifunctional structures are presented. Disconnection of the internal bonds results in illogical synthons because of the mismatch of charges in the patterns with an even number of C atoms between the functional groups. Three-membered heterocyclic rings are presented as an important class of illogical nucleophiles in the retrosynthesis of the 1,2-difunctional pattern. Retrosynthesis of the 1,6-dicarbonyl pattern by reconnection and retro-Birch reduction of the aromatic building block is related to chemoselective Birch reduction and ozonolysis in the synthetic route. The retrosynthesis and synthesis of salbutamol and asymmetric synthesis of (−)-frontalin are presented.
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Šunjić, V., Petrović Peroković, V. (2016). Illogical Disconnections with Participation of Two Groups. In: Organic Chemistry from Retrosynthesis to Asymmetric Synthesis. Springer, Cham. https://doi.org/10.1007/978-3-319-29926-6_5
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DOI: https://doi.org/10.1007/978-3-319-29926-6_5
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