title: Asymmetric Total Synthesis of the Putative Structure of Diplopyrone.
abstract: The first asymmetric total synthesis of the putative structure of diplopyrone was achieved in 17 linear steps starting from cis-1,4-butene-diol. The synthetic route features iodine-catalyzed tandem isomerization followed by C-O and C-C bond formation reaction strategy developed by our own group to construct the trans-2,6-disubstituted dihydropyran ring, asymmetric α-aminoxylation reaction, and Still-Gennari (Z)-selective olefination reactions. Careful comparison of1H and13C NMR spectroscopic data as well as investigation of the UV and circular dichroism spectrum in trifluoroethanol for compound 2 suggest that the putative structure for diplopyrone {6-[(1S)-1-hydroxyethyl]-2,4a(S),6(R),8a(S)-tetrahydropyran[3,2-b]pyran-2-one} requires revision.
authors.affiliation: Academy of Scientific and Innovative Research (AcSIR) , Mathura Road, New Delhi 110 025, India.
authors.forename: Saurabh
authors.identifier: 0000-0002-5413-2135
authors.initials: S
authors.lastname: Maity
authors.forename: Suresh
authors.initials: S
authors.lastname: Kanikarapu
authors.forename: Kanakaraju
authors.initials: K
authors.lastname: Marumudi
authors.forename: Ajit C
authors.initials: AC
authors.lastname: Kunwar
authors.affiliation: Academy of Scientific and Innovative Research (AcSIR) , Mathura Road, New Delhi 110 025, India.
authors.forename: Jhillu S
authors.initials: JS
authors.lastname: Yadav
authors.affiliation: Academy of Scientific and Innovative Research (AcSIR) , Mathura Road, New Delhi 110 025, India.
authors.forename: Debendra K
authors.identifier: 0000-0002-9515-826X
authors.initials: DK
authors.lastname: Mohapatra