title: Total Synthesis of the Marine Natural Product Solomonamide B Necessitates Stereochemical Revision.
abstract: The first total synthesis of the proposed structure of solomonamide B has been achieved. However, the (1)H and (13)C NMR spectral data of the synthesized compound was not exactly matching with that of the natural solomonamide B. This prompted us to revise the originally proposed structure, in particular, the stereochemistry of the nonpeptide part, which was confirmed by its total synthesis. During the course of the synthesis, we have developed an interesting hydroxy group directed Wacker oxidation of internal olefins in a macrocyclic setting.
authors.affiliation: Academy of Scientific and Innovative Research (AcSIR) , New Delhi 110 025, India.
authors.forename: K
authors.initials: K
authors.lastname: Kashinath
authors.affiliation: Academy of Scientific and Innovative Research (AcSIR) , New Delhi 110 025, India.
authors.forename: Gorakhnath R
authors.initials: GR
authors.lastname: Jachak
authors.forename: Paresh R
authors.initials: PR
authors.lastname: Athawale
authors.affiliation: Academy of Scientific and Innovative Research (AcSIR) , New Delhi 110 025, India.
authors.forename: Udaya Kiran
authors.initials: UK
authors.lastname: Marelli
authors.affiliation: Academy of Scientific and Innovative Research (AcSIR) , New Delhi 110 025, India.
authors.forename: Rajesh G
authors.initials: RG
authors.lastname: Gonnade
authors.affiliation: Academy of Scientific and Innovative Research (AcSIR) , New Delhi 110 025, India.
authors.forename: D Srinivasa
authors.initials: DS
authors.lastname: Reddy
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010456:Peptides, Cyclic / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D010456:Peptides, Cyclic; C558621:solomonamide B