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Issue 37, 2016
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Substitution dependent stereoselective construction of bicyclic lactones and its application to the total synthesis of pyranopyran, tetraketide and polyrhacitide A

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Abstract

A novel bicyclization strategy has been developed for the stereoselective synthesis of bicyclic lactones, i.e. 7-aryl or alkyl-2,6-dioxabicyclo[3.3.1]nonan-3-ones through a domino cyclization of (R)-3-hydroxyhex-5-enoic acid with an aldehyde in the presence of 10 mol% trimethylsilyltriflate under mild conditions. The salient features of this methodology are high yields, excellent selectivity, low catalyst loading and faster reaction times. This method has been successfully applied to the total synthesis of pyranopyran, tetraketide and polyrhacitide A.

Graphical abstract: Substitution dependent stereoselective construction of bicyclic lactones and its application to the total synthesis of pyranopyran, tetraketide and polyrhacitide A

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Publication details

The article was received on 05 Aug 2016, accepted on 23 Aug 2016 and first published on 25 Aug 2016


Article type: Paper
DOI: 10.1039/C6OB01686C
Citation: Org. Biomol. Chem., 2016,14, 8832-8837
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    Substitution dependent stereoselective construction of bicyclic lactones and its application to the total synthesis of pyranopyran, tetraketide and polyrhacitide A

    B. V. Subba Reddy, D. O. Biradar, Y. Vikram Reddy, J. S. Yadav, K. K. Singarapu and B. Sridhar, Org. Biomol. Chem., 2016, 14, 8832
    DOI: 10.1039/C6OB01686C

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