Abstract
Abstract The stereoselective synthesis of a carboxylic acid ester corresponding to the C1–C16 fragment of bryostatin, with 4-methoxybenzyl (PMB) protection for the 7-hydroxyl group, is reported. The key steps included a Horner-Wadsworth-Emmons reaction between (5R)-3-[(E)-2-tri-isopropylsilyloxyethylidene]-6-(4-methoxybenzyloxy)-5-triethylsilyloxyhexanal and dimethyl (4S,6R,8S)-10-hydroxy-6,8-di-O-isopropylidene-4-(4-methoxybenzyloxy)-3,3-dimethyl-2-oxodecan-1-yl phosphonate, that gave the corresponding (E)-alkene, followed by selective cleavage of the triethylsilyl ether and cyclisation to give the required 2,6-cis-disubstituted 4-[(Z)-tri-isopropylsilyloxyethylide]tetrahydropyran. Oxidation of the primary alcohol gave the corresponding carboxylic acid that was converted into the required allyl ester.
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