title: Total Synthesis of the Proposed Structure of Maltepolide C.
abstract: The first total synthesis of the proposed structure of cytotoxic macrolide maltepolide C has been achieved via an E-selective intramolecular Heck cyclization as a key step. Other key features of the synthesis are Z-selective Wittig olefination, Sharpless asymmetric dihydroxylation followed by Williamson-type cyclo-etherification, Brown asymmetric allylation, and Noyori reduction of an alkynone. Detailed NMR study confirms the structure and stereochemistry of the synthetic maltepolide C unambiguously. However, the deviation of the spectra of the synthetic maltepolide C from those of the natural maltepolide C indicates a possible error in the original structural assignment.
authors.affiliation: Organic and Biomolecular Chemistry Division and ‡Centre for NMR & Structural Chemistry, CSIR-Indian Institute of Chemical Technology , Tarnaka, Hyderabad 500007, India.
authors.forename: K Nageswara
authors.initials: KN
authors.lastname: Rao
authors.affiliation: Organic and Biomolecular Chemistry Division and ‡Centre for NMR & Structural Chemistry, CSIR-Indian Institute of Chemical Technology , Tarnaka, Hyderabad 500007, India.
authors.forename: M
authors.initials: M
authors.lastname: Kanakaraju
authors.affiliation: Organic and Biomolecular Chemistry Division and ‡Centre for NMR & Structural Chemistry, CSIR-Indian Institute of Chemical Technology , Tarnaka, Hyderabad 500007, India.
authors.forename: A C
authors.initials: AC
authors.lastname: Kunwar
authors.affiliation: Organic and Biomolecular Chemistry Division and ‡Centre for NMR & Structural Chemistry, CSIR-Indian Institute of Chemical Technology , Tarnaka, Hyderabad 500007, India.
authors.forename: Subhash
authors.initials: S
authors.lastname: Ghosh