S1

Supporting Information

Transition Metal-Catalyzed Synthesis of Novel

Biologically Relevant Tryptophan Analogues

Bart C. J. van Esseveldt,[a] Floris L. van Delft,[a] Jan M. M. Smits,[b] René de Gelder,[b]

Hans E. Schoemaker,[c] and Floris P. J. T. Rutjes*[a]

[a] NSRIM, Department of Organic Chemistry, University of Nijmegen, Toernooiveld 1, NL-6525 ED

Nijmegen, The Netherlands [b] NSRIM, Department of Inorganic Chemistry, University of Nijmegen, Toernooiveld 1, NL-6525

ED Nijmegen, The Netherlands [c] DSM Research, Life Science Products, PO Box 18, NL-6160 Geleen, The Netherlands

S2

N CO2Me

NHBoc

Methyl 5-{2-[(tert-butoxycarbonyl)amino]phenyl}-3,4-dihydro-2H-2-pyrrolecarboxylate (18).

S3

N CO2Me

NH2Boc

1-(tert-Butyl) 2-methyl 5-(2-aminophenyl)-2,3-dihydro-1H-1,2-pyrroledicarboxylate (19).

S4

HN CO2MeBoc

O

Methyl 2-[(tert-butoxycarbonyl)amino]-5-oxo-5-phenylpentanoate (27).

S5

N CO2Me

NH Boc

Ac

1-(tert-butyl) 2-methyl 5-[2-(acetylamino)phenyl]-2,3-dihydro-1H-1,2-pyrroledicarboxylate (29).

S6

NO

ONH2

5-(2-Aminophenyl)-7,7a-dihydro-1H-pyrrolo[1,2-c][1,3]oxazol-3-one (30).

S7

HN CO2Me

NH

Boc

Methyl (2S)-2-[(tert-butoxycarbonyl)amino]-4-(1H-2-indolyl)butanoate (38).

S8

HN CO2MeBoc

NH

Methyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-(1H-2-indolyl)pentanoate (39).

S9

N CO2MeBoc

Boc

NH

Methyl (2S)-2-[di(tert-butoxycarbonyl)amino]-3-(1H-2-indolyl)propanoate (42).

S10

HN CO2MeBoc

NH

Methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-(1H-2-indolyl)propanoate (44).

S11

HN CO2MeTs

NH

Methyl 3-(1H-2-indolyl)-2-{[(4-methylphenyl)sulfonyl]amino}propanoate (47).

S12

HN CO2MeTs

O

Methyl (2S)-3-benzo[b]furan-2-yl-2-{[(4-methylphenyl)sulfonyl]amino}propanoate (51).