Asymmetric Total Synthesis of the Putative Structure of Diplopyrone

Autor:	Kanakaraju Marumudi, Debendra K. Mohapatra, J. S. Yadav, Ajit C. Kunwar, Suresh Kanikarapu, Saurabh Maity
Rok vydání:	2017
Předmět:	Circular dichroism Tandem 010405 organic chemistry Stereochemistry Dihydropyran Organic Chemistry Structure (category theory) Total synthesis Carbon-13 NMR 010402 general chemistry Ring (chemistry) 01 natural sciences 0104 chemical sciences chemistry.chemical_compound chemistry Isomerization
Zdroj:	The Journal of Organic Chemistry. 82:4561-4568
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.7b00086
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::b3d6569cd453256f0207bad4098dda95 https://doi.org/10.1021/acs.joc.7b00086 Zobrazit plný text záznamu