Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Asymmetric Total Synthesis of the Putative Structure of Diplopyrone

Asymmetric Total Synthesis of the Putative Structure of Diplopyrone
Jhillu S. Yadav, Ajit C. Kunwar, Suresh Kanikarapu, Kanakaraju Marumudi, Debendra K. Mohapatra, Saurabh Maity
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00086

DOI: 10.1021/acs.joc.7b00086

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