- Catalyst-Controlled Transannular Polyketide Cyclization Cascades: Selective Folding of Macrocyclic Polyketides
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The biomimetic synthesis of aromatic polyketides from macrocyclic substrates by means of catalyst-controlled transannular cyclization cascades is described. The macrocyclic substrates, which feature increased stability and fewer conformational states, were thereby transformed into several distinct polyketide scaffolds. The catalyst-controlled transannular cyclizations selectively led to aromatic polyketides with a defined folding and oxygenation pattern, thus emulating β-keto-processing steps of polyketide biosynthesis.
- Raps, Felix C.,F?seke, Vincent C.,H?ussinger, Daniel,Sparr, Christof
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supporting information
p. 18390 - 18394
(2020/08/25)
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- Dimeric Naphthoquinones, 17. Synthesis of Stypandrone and Dianellinone
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The naphthoquinone stypandrone (2b) ist synthesized via the intermediates 5a, 6a and 6b.Selective monoalkylation of its hydroquinone yields the monoether 12b, which, on phenol oxidation and oxidative dealkylation, leads to 13 and dianellinone (2a).The synthesis confirms the 3,3'-dimerisation of the natural product. - Keywords: Naphthoquinones, Stypandrone, Dianellinone, Phenol Oxidation
- Laatsch, Hartmut
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p. 377 - 385
(2007/10/02)
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