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Issue 39, 2019
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Expeditious diastereoselective synthesis of medium ring heterocycle-fused chromenes via tandem 8/9-endo-dig and 8-exo-dig hydroalkoxylation-formal-[4 + 2] cycloaddition

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Abstract

The first examples of highly diastereoselective tandem 8/9-endo-dig and 8-exo-dig hydroalkoxylation-formal-[4 + 2] cycloaddition are described for the synthesis of medium ring heterocycle-fused chromenes. TMS-alkynols preferred the exo-dig mode of hydroalkoxylation over the endo-dig mode leading to spiro-cyclic chromenes. The method could be used for the synthesis of linearly-fused ladder-like polyethers. A thia-heterocycle-fused chromene could be transformed into a complex bridged tricyclic ketal by a tandem carbene-insertion-[2,3]-sigmatropic shift.

Graphical abstract: Expeditious diastereoselective synthesis of medium ring heterocycle-fused chromenes via tandem 8/9-endo-dig and 8-exo-dig hydroalkoxylation-formal-[4 + 2] cycloaddition

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Publication details

The article was received on 14 Aug 2019, accepted on 18 Sep 2019 and first published on 18 Sep 2019


Article type: Communication
DOI: 10.1039/C9OB02030F
Org. Biomol. Chem., 2019,17, 8806-8810

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    Expeditious diastereoselective synthesis of medium ring heterocycle-fused chromenes via tandem 8/9-endo-dig and 8-exo-dig hydroalkoxylation-formal-[4 + 2] cycloaddition

    S. J. Gharpure, S. K. Nanda and D. J. Fartade, Org. Biomol. Chem., 2019, 17, 8806
    DOI: 10.1039/C9OB02030F

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