American Chemical Society
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Iodocyclization and Prins-Type Macrocyclization: An Efficient Formal Synthesis of Leucascandrolide A

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journal contribution
posted on 2011-04-01, 00:00 authored by J. S. Yadav, Manas R. Pattanayak, Pragna P. Das, Debendra K. Mohapatra
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.