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In this communication, we introduce our retrosynthetic approach to the synthesis of roseophilin. An interesting, new Wittig/aldol methodology is described. Also discussed is macrocyclization of an azide acid to form an unsaturated lactam.
Treatment of carboxylic acids with boron trichloride followed by addition of alcohol provides the carboxylic ester. This esterification, following BCl 3 ether or ester O C cleavage reaction conditions, proceeds cleanly in good yields with most substrates. Cleavage of benzyl esters with boron trichloride then treating with methanol affords the methyl ester.
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