Abstract
A useful approach for the direct enantioselective synthesis of ( S)- N-Boc-protected α-indol-3-ylglycinols from vinyl indoles using the Sharpless asymmetric aminohydroxylation reaction, with enantioselectivities of up to 94% and isolated yields of up to 65%, is described. Expeditious enantioselective syntheses of hamacanthin A and dragmacidin A have been achieved using the corresponding N-Boc-protected α-6-bromo-indol-3-ylglycinol as the key intermediate. Furthermore, the absolute stereochemistry of cis- and trans-dihydrohamacanthin A has been determined through the enantioselective total synthesis of the unnatural enantiomers.
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