P-Methoxybenzylmagnesium chloride

In analogy to a synthesis of morphinans from 1,2,3,4,5,6,7,8-octahy-droisoquinolines by Grewe,(22,23) May and Fry<24) prepared benzomorphans (Scheme 4.9). Treatment of 3,4-dialkyl or 4-alkylpyridinium methiodides with either benzyl or p-methoxybenzylmagnesium chloride in ether readily gives... 

A total synthesis of (-)-anisomycin (1) from malimide has been achieved by a highly regio and trans stereoselective reductive alkylation of (S)-M,0-dibenzyl malimide 117 (Scheme 14) [85]. Reductive alkylation of (S)-lM,0-dibenzyl malimide 117, prepared from (S)-malic acid [86], with p-methoxybenzylmagnesium chloride gave the a-hydroxylactam 118 as a di-astereomeric mixture. Hydroxylactam 118 in the presence of 3 equivalents of boron trifluoride etherate was reduced with excess of triethylsilane to yield predominantly trans-119 in 94.8% yield. Catalytic hydrogenation of 119 afforded 120 in quantitative yield which was reduced to pyrrolidine 121 in 90%... 

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