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• W2342376833 endingPage "4261" @default.
• W2342376833 startingPage "4252" @default.
• W2342376833 abstract "The formal total synthesis of both the enantiomers of cyclophellitol and conduritol-B and synthesis of conduramine-B derivative have been achieved from a common intermediate, obtained by regio- and stereoselective vicinal functionalization of a diene utilizing an intramolecular sulfinyl group as a nucleophile, followed by stereoselective preparation of an allylic sulfide by reaction of vinylzinc bromide with an electrophilic α-chloro sulfide, and last by ring-closing metathesis reaction as the key steps. The sulfoxide, sulfilimine, and sulfur ylid prepared from this common intermediate have been transformed into derivatives of conduritol-B, conduramine-B, and (-)-cyclophellitol, respectively. The silyl sulfide was converted via sila-Pummerer rearrangement, hydrolysis, and reduction in an one-pot operation to a hydroxymethyl group. [2,3]-Wittig-Still rearrangement was employed for the synthesis of (+)-cyclophellitol. The potential utility of sulfur intermediates as nucleophilic and electrophilic partners in total synthesis is elegantly demonstrated." @default.
• W2342376833 created "2016-06-24" @default.
• W2342376833 creator A5031662314 @default.
• W2342376833 creator A5060282929 @default.
• W2342376833 creator A5069130336 @default.
• W2342376833 date "2016-04-28" @default.
• W2342376833 modified "2023-09-24" @default.
• W2342376833 title "Stereoselective Formal Synthesis of (+)- and (−)-Cyclophellitol and (−)-Conduritol-B and Synthesis of (−)-Conduramine-B Derivative Using a Sulfinyl Moiety for C–O Bond Formation and α-Chloro Sulfide for C–C Bond Formation" @default.
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• W2342376833 doi "https://doi.org/10.1021/acs.joc.6b00616" @default.
• W2342376833 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/27096579" @default.
• W2342376833 hasPublicationYear "2016" @default.
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