Asymmetric Synthesis of (−)-Martinellic Acid
2013-04-19T00:00:00Z (GMT) by
A high-yielding total asymmetric synthesis of (−)-martinellic acid is reported. The conjugate addition of lithium (<i>R</i>)-<i>N</i>-allyl-<i>N</i>-(α-methyl-4-methoxybenzyl)amide to <i>tert</i>-butyl (<i>E</i>)-3-[2′-(<i>N</i>,<i>N</i>-diallylamino)-5′-bromophenyl]propenoate and alkylation of the resultant β-amino ester have been used as the key steps to install the C(9b) and C(3a) stereogenic centers, respectively, and a highly diastereoselective Wittig reaction/intramolecular Michael addition was then used to create the C(4) stereogenic center within this tricyclic molecular architecture.
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