A fully synthetic route to the papulacandins. Stereospecific spiroacetalization of a C-1-arylated methyl glycoside

Add time:07/11/2019    Source:sciencedirect.com

Lewis acid-catalyzed, hetero Diels-Alder reaction of (E)-1-methoxy-3-trimethylsilyloxy-1,3-butadiene with 6-benzoyloxymethyl-2,4-dibenzyloxy benzaldehyde afforded 2-(6-benzoyloxymethyl-2,4-dibenzyloxyphenyl)-2,3-dihydro-4H-pyran-4-one. This was converted into a derivative of papulacandin D by a stereospecific, spiroacetalization of a C-1 methoxylated aryl glycoside, [3,5-dibenzoyloxy-(methyl 3-O-acetyl-4,6-di-O-benzoyl-dl-glucopyranosid-1-yl)phenyl]methyl benzoate.

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