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Synlett

Volumn , Issue 1, 2007, Pages 99-102

First stereoselective synthesis of a Tyr-Tyr E-alkene isostere

(3) Bandur, Nina G a Harms, Klaus a Koert, Ulrich a

a PHILIPPS UNIVERSITY MARBURG (Germany)

Author keywords

Aldol reaction; Dipeptide isostere; E alkene; Julia Kocie ski olefination; Tyrosine

Indexed keywords

ALDEHYDE; ALKENE; TYROSINE;

ALDOL REACTION; ARTICLE; ATOM; CHEMICAL BOND; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; OLEFINATION; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 33846420210 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2006-956456 Document Type: Article

Times cited : (7)

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21
- 33846428341
- Analytical Data of Sulfone 4. Rf, 0.11 (cHex-TBME, 2:1, α]D27-9.1 (c 1.23, CHCl3, 1H NMR (300 MHz, CDCl3, δ, 7.67-7.53 (m, 5 H, 7.11-7.03 (m, 2 H, 6.99-6.89 (m, 3 H, 4.84-4.67 (m, 1 H, 4.13 (dd, J, 15.3, 9.1 Hz, 1 H, 3.97 (dd, J, 15.3, 3.6 Hz, 1 H, 3.11 (dd, J, 13.8, 7.0 Hz, 1 H, 3.04 (dd, J, 13.8, 6.8 Hz, 1 H, 1.33 (s, 9 H, 13C NMR (75 MHz, CDCl3, δ, 156.8 (q, J, 38 Hz, 155.1, 153.6, 131.7, 129.75 (2 C, 129.72 (2 C, 129.3, 125.1 (2 C, 124.6 (2 C, 78.8, 57.5, 47.5, 38.7, 28.8 (3 C, IR (film, v, 3323 (m, 2982 (m, 2932 (w, 1703 (s, 1559 (m, 1508 (m, 1354 (s, 1220 (m, 1156 (s, 899 (w, 879 (w, 764 (m, 689 (w, 639 (m, 522 (m) cm-1. HRMS ESI, m/z calcd for C22H24F3N 5NaO4S [M, Na, 534.1393; found: 534
- +]: 534.1393; found: 534.1401.

22
- 33846456543
- 2 (1 atm), MeOH-EtOAc (1:1), 3 h, 99%; 4. TBDPSCl, imidazole, DMF, 0 °C to r.t, 12 h, 89%.
- 2 (1 atm), MeOH-EtOAc (1:1), 3 h, 99%; 4. TBDPSCl, imidazole, DMF, 0 °C to r.t, 12 h, 89%.

23
- 33846440801
- Preparation of Compound 6. A solution of 5 (7.02 mmol, 3.96 g) in CH2Cl2 (40 mL) was cooled to 0 °C and TiCl4 (7.72 mmol, 0.85 mL) was added dropwise. After 5 min, diisopropylethyl amine (DIPEA, 8.01 mmol, 1.4 mL) was added whereupon the solution turned dark purple. After the mixture was stirred at 0 °C for 1 h a solution of 1,3,5-trioxane (8.01 mmol, 0.72 g) in CH2Cl2 (5 mL) was added, followed by TiCl4 (7.37 mmol, 0.81 mL, The mixture was stirred for 3 h at 0-10 °C. Then, sat. NH4Cl solution (50 mL) was added and the layers were separated. After extraction with additional CH2Cl 2 (3 × 50 mL) the organic layers were pooled and washed subsequently with H2O (2 × 25 mL) and brine (50 mL, After drying with Na2SO4 and evaporation of solvents the residue was purified by flash column chromatography on silica 300 g, TBME-pentane
- +]: 500.2228; found: 500.2229.

24
- 33846420546
- No other stereoisomer was detected in the NMR spectra. For the assignment of the stereochemistry of 6, see Figure 1.
- No other stereoisomer was detected in the NMR spectra. For the assignment of the stereochemistry of 6, see Figure 1.

25
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- Evans, D.A.¹ Urpi, F.² Somers, T.C.³ Clark, J.S.⁴ Bilodeau, M.T.⁵

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27
- 33846458929
- int = 0.0390), R1 = 0.0265, wR2 = 0.0686 (all data).
- int = 0.0390), R1 = 0.0265, wR2 = 0.0686 (all data).

28
- 33846416129
- Preparation of Compound 9. A solution of sulfone 4 (0.17 mmol, 85 mg) in 1,2-dimethoxyethane (DME, 1 mL) was cooled to -78 °C and NaHMDS (2 M in THF, 0.37 mmol, 0.18 mL) was added. The resulting yellow solution was stirred at -78 °C for 30 min and aldehyde 8 dissolved in DME (0.5 mL) was added. The solution allowed to warm to r.t. overnight. Then phosphate buffer (1 M, 2 mL) and TBME (4 mL) were added. After the layers were separated the aqueous layer was extracted with additional TBME (3 × 4 mL, The combined organic extracts were dried with Na2SO4 and after evaporation of solvents the residue was purified by flash column chromatography (8 g, TBME-pentane, 1:10) followed by a second chromatography 8 g, acetone-pentane, 1:10, The pure product 9 was obtained as a colorless oil. The determination of the E/Z selectivity of 2.3:1 and the separation of the isomers was done after THP deprotection affording compound 10. E-Isomer: R
- +]: 544.2645; found: 544.2651.

29
- 0000307530
- De Mico, A.; Margarita, R.; Parlani, L.; Vescovi, A.; Piancatelli, G. J. Org. Chem. 1997, 62, 6974.
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- De Mico, A.¹ Margarita, R.² Parlani, L.³ Vescovi, A.⁴ Piancatelli, G.⁵

30
- 33846405192
- Analytical Data of Compound 11. Rf, 0.24 (c-Hex-EtOAc, 1:1, α]D19 -30.7 (c 0.32, CHCl3, 1H NMR (500 MHz, 343 K, DMSO-d 6, δ, 11.98 (br s, 1 H, 7.85 (pd, J, 7.6 Hz, 2 H, 7.63 (pd, J, 7.6 Hz, 2 H, 7.40 (pt, J, 7.4 Hz, 2 H, 7.31 (pt, J, 7.4 Hz, 2 H, 7.25-7.11 (m, 1 H, 7.05 (pd, J, 8.3 Hz, 2 H, 7.03-6.97 (m, 2 H, 6.83 (pd, J, 8.5 Hz, 2 H, 6.78 (pd, J, 8.5 Hz, 2 H, 5.57-5.42 (m, 2 H, 4.28-4.17 (m, 2 H, 4.15-4.07 (m, 1 H, 4.14 (t, J, 6.8 Hz, 3.17-3.06 (m, 1 H, 2.90 (dd, J, 13.7, 7.6 Hz, 1 H, 2.69-2.57 (m, 3 H, 1.26 (s, 9H, 1.22 (s, 9 H, 13C NMR (500 MHz, 343 K, DMSO-d6, δ, 177.4, 153.2, 153.1 (2 C, 143.61, 143.59, 140.4 (2 C, 133.1, 132.64, 132.58, 129.3 (2 C, 129.1 (2 C, 127.3, 127.1 (2 C, 126.6 (2 C, 124.7 (2 C, 122.7 (2 C, 122.6 (2 C, 119.6 2 C, 77.2, 77.1
- +]: 684.3296; found: 684.3313.

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