title: Total synthesis of the macrocyclic N-Methyl enamides palmyrolide A and 2S-sanctolide A.
abstract: Full details of the total syntheses of the initially reported and revised structures of the neuroprotective agent palmyrolide A are reported. The key macrocyclization step was achieved using a sequential ring-closing metathesis/olefin isomerization reaction. Furthermore, the total synthesis of the related macrolide (2S)-sanctolide A is reported. The synthesis used key elements from the synthesis of palmyrolide A, including the RCM/olefin isomerization sequence. The synthetic work described herein serves to facilitate the assignment of stereochemistry of the natural product sanctolide A and demonstrates the utility of this approach for the synthesis of macrocyclic tertiary enamide natural products.
authors.affiliation: Maurice Wilkins Centre for Molecular Biodiscovery, School of Chemical Sciences, University of Auckland , 23 Symonds Street, Auckland 1142, New Zealand.
authors.forename: Andrew D
authors.initials: AD
authors.lastname: Wadsworth
authors.forename: Daniel P
authors.initials: DP
authors.lastname: Furkert
authors.forename: Margaret A
authors.initials: MA
authors.lastname: Brimble
mesh_terms: D000475:Alkenes / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D007536:Isomerism; D047028:Macrocyclic Compounds / Q000138:chemical synthesis*; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C000599373:2S-sanctolide A; D000475:Alkenes; D001688:Biological Products; D047028:Macrocyclic Compounds; D018942:Macrolides; C572829:palmyrolide A