Iodocyclization and Prins-type macrocyclization: an efficient formal synthesis of leucascandrolide A |
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Authors: | Yadav J S Pattanayak Manas R Das Pragna P Mohapatra Debendra K |
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Affiliation: | Organic Chemistry Division I, Indian Institute of Chemical Technology, CSIR, Hyderabad 500 607, India. |
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Abstract: | The formal total synthesis of leucascandrolide A has been achieved in 20 steps from a known epoxide with an overall yield of 11.5% following a recently developed strategy for the construction of trans-2,6-disubstituted-3,4-dihydropyrans and a Lewis acid catalyzed intramolecular Prins-cyclization of an aldehydic homoallylic alcohol to generate the tetrahydropyran ring with three stereogenic centers and macrocycle concomitantly. |
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