A Stereoselective Synthesis of (+)-Piscidic Acid and Cimicifugic Acid L

作者:Miranda Vanessa; Maycock Christopher D; Ventura M Rita*
来源:European Journal of Organic Chemistry, 2015, 2015(34): 7529-7533.
DOI:10.1002/ejoc.201501002

摘要

Alkylation of the lithium enolate of (2S, 3S, 5S, 6S)-dimethoxy-2,3-dimethyl-1,4-dioxane-5,6-dithiocarboxylate using 4-benzyloxybenzyl bromide stereoselectively gave two new stereogenic centres with the carboxylate groups in a cis relationship. Hydrolytic deprotection of this intermediate produced the natural product (+)-piscidic acid. Installation of a cinnamic acid ester at the secondary hydroxy group was followed by selective deprotection to give a mixture of cis/trans cinnamates in a 3: 1 ratio. Finally, the natural product cimicifugic acid L was obtained.

  • 出版日期2015-12