Synthesis of Chromones from 1,1-Diacylcyclopropanes: Toward the Synthesis of Bromophycoic Acid E.

A tandem deprotection-cyclization reaction of 1,1-diacylcyclopropanes is described which allows rapid access to structurally diverse 2,3-disubstituted chromones in good yields, and with straightforward purification. The utility of this reaction is showcased by the construction of the potent antibacterial marine natural product bromophycoic acid E scaffold.

Selective Mono-allylation of 1,3-Diketones and Their Use in the Synthesis of 3-Allyl Chromones and Benzannulated 6,5-Bicyclic Ketals.

The selective mono-allylation of 1,3-diketone containing compounds is described. The reaction proceeds under mild reaction conditions and in moderate to high yield (66-99 %). Using this procedure to access the key mono-allylated intermediate, the hitherto difficult to access 3-allyl chromones were synthesized in excellent yield (87-98 %). Finally, the utility of this newly developed procedure was showcased through the rapid synthesis of the scaffold of the xyloketal family of natural products.