SCHEDULED MAINTENANCE
Synthetic approaches to the alkaloids of the ancistrocladaceae. Part 3. The total synthesis of (–)-ancistrocladinine: control of the diastereoisomer excess in the synthesis of axially chiral biaryls
Abstract
The total synthesis of the naphthylisoquinoline alkaloid (–)-ancistrocladinine[(–)-(S,3S)-6-hydroxy-5-(4,5-dimethoxy-2-methyl-1-naphthyl)-8-methoxy-3,4-dihydro-1,3-dimethylisoquinoline] is described. The key step was the construction of the disymmetric biaryl linkage by a coupling between the Grignard reagent derived from 2-(3-benzyloxy-2-bromo-5-methoxyphenyl)-1,3-dioxane and (+)(4S,5S)-4-methoxymethyl-5-phenyl-2-(1,4,5-trimethoxy-2-naphthyl)-4,5-dihydroxazole. The reactions between the last-mentioned compound and a variety of 2,6-disubstituted phenyl Grignard reagents have been investigated and an attempt has been made to delineate the factors which control the diastereoisomeric excess.
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