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A protocol for general diastereoselective tandem dihydroxylation followed by SN2 cyclization was developed for the convenient and efficient synthesis of cis- and trans-2,6-disubstituted tetrahydropyrans from ζ-mesyloxy α,β-unsaturated esters. The application… Click to show full abstract
A protocol for general diastereoselective tandem dihydroxylation followed by SN2 cyclization was developed for the convenient and efficient synthesis of cis- and trans-2,6-disubstituted tetrahydropyrans from ζ-mesyloxy α,β-unsaturated esters. The application of this novel method was demonstrated through the concise formal synthesis of (+)-muconin, a nonclassical acetogenin, with sequential THP-THF ring formation.
Keywords:
synthesis muconin;
general diastereoselective;
trans disubstituted;
disubstituted tetrahydropyrans;
cis trans;
synthesis
Journal Title: Organic letters
Year Published: 2018
Link to full text (if available)
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Journal Title: Organic letters
Year Published: 2018
Link to full text (if available)
Share on Social Media: Sign Up to like & get
recommendations!