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2005
Other bioactive products
U 1300
Asymmetric Synthesis of Pyrrolidinoindolines. Application for the Practical Total
of (-)-Phenserine. — The diastereoselective dialkylation of ditriflate (II)
12- 246 Synthesis
with oxindole enolates, having alkyl substituents at C-3, proceeds with high facial selectivity. The main diastereomer is cleaved to give 2 equiv. of the corresponding enantiopure 3-alkyl-3-(2-oxoethyl)oxindole like (VIII), which, in one double reductive
amination step is converted to enantiopure pyrrolidinoindolines, cf. (X). Using this
strategy, enantiopure (-)-phenserine (XI) is prepared on a multigram scale in 43% overall yield from (VI). — (HUANG, A.; KODANKO, J. J.; OVERMAN*, L. E.; J. Am.
Chem. Soc. 126 (2004) 43, 14043-14053; Dep. Chem., Univ. Calif., Irvine, CA 92697,
USA; Eng.) — Bartels
2005
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