Synthesis of substituted-(l)-tryptophanols from an enantiomerically pure aziridine-2-methanol

D K Pyun; C H Lee; H J Ha; C S Park; J W Chang; W K Lee

doi:10.1021/ol016861+

Synthesis of substituted-(l)-tryptophanols from an enantiomerically pure aziridine-2-methanol

Org Lett. 2001 Dec 27;3(26):4197-9. doi: 10.1021/ol016861+.

Authors

D K Pyun¹, C H Lee, H J Ha, C S Park, J W Chang, W K Lee

Affiliation

¹ Department of Chemistry, Sogang University, Seoul 121-742, Korea.

PMID: 11784176
DOI: 10.1021/ol016861+

Abstract

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]