title: Synthesis of palmyrolide A and its cis-isomer and mechanistic insight into trans-cis isomerisation of the enamide macrocycle.
abstract: 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.
authors.affiliation: Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. HomiBhabha Road, Pune, 411008, India.
authors.forename: Satish Chandra
authors.initials: SC
authors.lastname: Philkhana
authors.forename: B
authors.initials: B
authors.lastname: Seetharamsingh
authors.forename: Yuvraj B
authors.initials: YB
authors.lastname: Dangat
authors.forename: Kumar
authors.initials: K
authors.lastname: Vanka
authors.forename: D Srinivasa
authors.initials: DS
authors.lastname: Reddy
mesh_terms: D000080462:Acyclic Monoterpenes; D000447:Aldehydes / Q000737:chemistry; D007536:Isomerism; D018942:Macrolides / Q000737:chemistry*; D039821:Monoterpenes / Q000737:chemistry
chemical_list: D000080462:Acyclic Monoterpenes; D000447:Aldehydes; D018942:Macrolides; D039821:Monoterpenes; C572829:palmyrolide A; C108217:citronellal