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A Stereoselective Synthesis of (+)‐Piscidic Acid and Cimicifugic Acid L
Author(s) -
Miranda Vanessa,
Maycock Christopher D.,
Ventura M. Rita
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501002
Subject(s) - chemistry , stereocenter , cinnamates , stereoselectivity , hydrolysis , alkylation , natural product , bromide , carboxylate , cinnamic acid , organic chemistry , lithium (medication) , stereochemistry , medicinal chemistry , catalysis , enantioselective synthesis , medicine , endocrinology
Alkylation of the lithium enolate of (2 S ,3 S ,5 S ,6 S )‐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.