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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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Article information


Submitted
05 Aug 2016
Accepted
23 Aug 2016
First published
25 Aug 2016

Org. Biomol. Chem., 2016,14, 8832-8837
Article type
Paper

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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