An efficient stereoselective synthesis of Z-(2S)- and Z-(2R)-2-tert-butoxycarbonylamino-6-hydroxyhex-4-enoic acid, key intermediates in the synthesis of (2S,4S,5R)-(−)- and (2R,4R,5S)-(+)-bulgecinine

Add time:08/22/2019    Source:sciencedirect.com

A concise, scaleable route to both isomers of Z-2-tert-butoxycarbonylamino-6-hydroxyhex-4-enoic acid from 2-butyne-1,4-diol, utilizing l- and d-acylase enzymes is presented. These intermediates were readily converted to multigram quantities of N-Boc-(2S,4S,5R)- and N-Boc-(2R,4R,5S)-bulgecinine.

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