Synthesis of (3aS-cis)-(−)- and (3aR-cis)-(+)-debromoflustramine B

Add time:08/19/2019    Source:sciencedirect.com

A synthesis of the (3aS-cis)-(−)- and (3aR-cis)-(+)-enantiomers of debromoflustramine B 1 is reported. The synthesis involves the chromatographic separation of the corresponding (−)- and (+)-N-phenylethyl lactams 10 and 11, obtained by the reaction of racemic lactone 6 with (S)-(−)-1-phenylethylamine, followed by hydrolysis to give both enantiomers of 6 with very high enantiomeric excesses. The lactamization of (−)-6 gives (−)-7, which was converted to (−)-1 by reduction with LiAlH4 without racemization. Optically active (+)-1 was similarly prepared from (+)-6. The absolute configurations were established by comparison with the known negative Cotton effect of (3aS-cis)-(−)-physostigmine.

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