Organic Letters 2005-04-14

Synthesis of a C20-C26 segment of superstolide A by addition of a chiral allenylzinc reagent to (R)-N-boc alaninal.

James A Marshall, James J Mulhearn

Index: Org. Lett. 7 , 1593-1596, (2005)

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Abstract

[reaction: see text] Additions of chiral allenylzinc and indium reagents to N-Boc alaninal were examined as a possible route to a C20-C26 segment of superstolide A. Allenylzinc reagents, prepared in situ by palladiozincation of (R)- and (S)-5-pivalyloxy-3-butyn-2-ol mesylate, showed excellent reagent control to afford the anti,syn and anti,anti diastereomers as the nearly exclusive adducts.