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2-Hydroxy-4-methoxybenzaldehyde (673-22-3) 's Synthetic route

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Enantioselective total synthesis of (-)-blennolide A

Tietze, Lutz F.  Ma, Ling  Reiner, Johannes R.  Jackenkroll, Stefan  Heidemann, Sven

Blennolide A can be synthesized through an enantioselective domino-Wacker/carbonylation/methoxylation reaction of 7 a with 96 % ee and an enantioselective Wacker oxidation of 7 b with 89 % ee. Further transformations led to the α,β-unsaturated ester (E)-17, which was subjected to a highly selective Michael addition, introducing a methyl group to give 18 a. After a threefold oxidation and an intramolecular acylation, the tetrahydroxanthenone 4 was obtained, which could be transformed into (-)-blennolide A (ent-1) in a few steps. Domino effect: An enantioselective domino-Wacker/carbonylation/methoxylation process and an enantioselective Wacker oxidation are the key steps in the first total synthesis of the fungal metabolite blennolide A (see scheme). Copyright

Facile C-S Bond Cleavage of Aryl Sulfoxides Promoted by Bronsted Acid

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