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Asymmetric Total Synthesis of the Putative Structure of Diplopyrone. 2017

Saurabh Maity, and Suresh Kanikarapu, and Kanakaraju Marumudi, and Ajit C Kunwar, and Jhillu S Yadav, and Debendra K Mohapatra
Academy of Scientific and Innovative Research (AcSIR) , Mathura Road, New Delhi 110 025, India.

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 of 1H and 13C 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.

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