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- W2951991036 abstract "The a-alkylation (allylationipropargylation) of 3,5-dibromo-4-hydroxybenzaldehyde 1 and the corresponding acetophenone 2 re sult s in the formation of aryl-aryl coupled product by loss of formyl groups, aryl-aryl ether and aryloxy acetone in addi tion to the expected 0allyl! propargyl ethers. While the thermal Claisen rearrangement of allyl ethers 1 and 2 furnishes the C-allyl products by loss of bromine, the propargyl ether 7 surprisingly resisted rearran gement and underwent oxidation to yield the corresponding carboxyl ic acid. Sponges of the order Verongeda are known to elabo rate a variety of pharmacologically active dibromotyro sine based natural products. Most of the metabolites are found with either oxazolidone rings or spiroxazoline systems or both. I Synthesis of such metabolites is chaJlenging and of current interest. 3,5-Dibromo-4-hydroxybenzaldehyde 1 and the corresponding acetophenone 2 are found to be the key synthons for a number of dibromotyrosine based natural products. 2 .3 In fact compound 1 was iso lated from the chlorofonn extract of the marine annelid Thelepus setosus by Higa et at. 4.5" @default.
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- W2951991036 date "2002-07-01" @default.
- W2951991036 modified "2023-09-28" @default.
- W2951991036 title "Interesting product formation during O-alkylation and subsequent rearrangement of two building blocks of dibromotyrosine based natural products" @default.
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