Concise and protecting-group free synthesis of ent-palmyrolide A and (-)-cis-palmyrolide A were achieved starting from commercially available (S)-citronellal. The key fragment of palmyrolide A, "(5S,7S)-7-hydroxy-5,8,8-trimethylnonanamide", which makes up the most challenging part of the target molecule, was prepared in just three steps. A plausible mechanism for the trans-cis isomerization of the double bond in the macrocycle has been investigated.
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Synthesis and biological evaluation of palmyrolide A macrocycles as sodium channel blockers towards neuroprotection.
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Maurice Wilkins Centre for Molecular Biodiscovery, School of Chemical Sciences, University of Auckland, 23 Symonds Street, Auckland 1142, New Zealand.
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Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces, New Mexico 88003, USA.
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