Synthesis of substituted-(l)-tryptophanols from an enantiomerically pure aziridine-2-methanol.
Enantiomerically pure (l)-tryptophanol (5) was synthesized from 4(R)-iodomethyl-2-oxazolidinone (2) and indolylmagnesium bromide in three steps (52% overall yield). Using this procedure, we also prepared various tryptophanols with substituent(s) on the indole ring. Furthermore, optically active 4(R)-iodomethyl-2-oxazolidinone was readily prepared from an enantiomerically pure aziridine-2(S)-methanol in high yield. [reaction: see text]
Pyun
D K
DK
Department of Chemistry, Sogang University, Seoul 121-742, Korea.
Lee
C H
CH
Ha
H J
HJ
Park
C S
CS
Chang
J W
JW
Lee
W K
WK