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Synlett 2005(16): 2469-2472
DOI: 10.1055/s-2005-917079
DOI: 10.1055/s-2005-917079
LETTER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Ring-A-Substituted Tryptophan by a Palladium-Catalyzed Heteroannulation Reaction
Further Information
Received
15 July 2005
Publication Date:
21 September 2005 (online)
Publication History
Publication Date:
21 September 2005 (online)
Abstract
Coupling of substituted o-iodoanilines with methyl (S)-2-N,N-di-tert-butoxycarbonyl-5-oxo-pentanoate, derived from glutamic acid, in DMF in the presence of palladium acetate and DABCO provides substituted tryptophans in good to excellent yields.
Key words
palladium-catalyzed heteroannulation - indole synthesis - substituted tryptophan
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Typical Experimental Procedure.
A solution of o-iodoaniline 3a (73.0 mg, 0.33 mmol), aldehyde 6 (104.0 mg, 0.30 mmol), and DABCO (101.0 mg, 0.9 mmol) and Pd(OAc)2 (3.4 mg, 0.015 mmol) in dry DMF (1.5 mL) was degassed. The reaction mixture was heated to 85 °C until the reaction was complete (usually 8-12 h). The reaction mixture was cooled to r.t. and was diluted with H2O. The aqueous phase was extracted with EtOAc and the combined organic phase was washed with brine, dried (Na2SO4), and evaporated to dryness under reduced pressure. Purification of crude product by flash column chromatography (silica gel, 20% EtOAc in heptane) provided the desired product 7 (101 mg, 81%; yellow oil). [α]D
23 -60.0 (c 1.00, CHCl3). IR (CHCl3): 3348, 2980, 2359, 1782, 1741, 1457, 1369, 1273, 1140, 1092, 852 cm-1. 1H NMR (300 MHz, CDCl3): δ = 8.45 (br s, 1 H), 7.58 (d, 1 H, J = 7.7 Hz), 7.34 (d, 1 H, J = 7.9 Hz), 7.15 (dt, 1 H, J = 1.2, 7.7 Hz), 7.09 (dt, 1 H, J = 1.2, 7.9 Hz), 6.98 (d, 1 H, J = 2.1 Hz), 5.20 (dd, 1 H, J = 4.7, 10.3 Hz), 3.77 (s, 3 H), 3.62 (dd, 1 H, J = 4.7, 14.9 Hz), 3.40 (dd, 1 H, J = 10.3, 14.9 Hz), 1.28 (s, 18 H). 13C NMR (75 MHz, CDCl3): δ = 171.1, 151.5, 136.3, 127.5, 123.2, 121.7, 119.2, 118.5, 111.2, 82.8, 58.9, 52.1, 27.6 (6 C), 25.8. MS (ESI): m/z = 441 [M + Na]. HRMS (ESI): m/z calcd for C22H30N2O6Na [M + Na]: 441.2002; found: 441.1975.
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References
l-Try was isolated in 10% yield under Baran’s modified conditions.