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.
Chemical Communications
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