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Volumn 20, Issue 5, 2009, Pages 527-530

First total synthesis of paecilodepsipeptide A

Author keywords

Macrolactamisation; Paecilodepsipeptide A; Total synthesis

Indexed keywords

EID: 62849124028 PISSN: 10018417 EISSN: None Source Type: Journal
DOI: 10.1016/j.cclet.2009.01.032 Document Type: Article

Times cited : (4)

References (16)

1
- 14844320177
- Blunt J.W., Copp B.R., and Munro M.H.G. Nat. Prod. Rep. 22 (2005) 15
- (2005) Nat. Prod. Rep. , vol.22 , pp. 15
- Blunt, J.W.¹ Copp, B.R.² Munro, M.H.G.³

2
- 33044492484
- White J.F., Bacon Jr. C.W., Hywel-Jones N.L., and Spatafora J.W. (Eds), Marcel Dekker, Inc., New York
- Isaka M., Kittakoop P., and Thebtaranonth Y. In: White J.F., Bacon Jr. C.W., Hywel-Jones N.L., and Spatafora J.W. (Eds). Clavicipitalean Fungi: Evolutionary Biology, Chemistry, Biocontrol, and Cultural Impacts (2003), Marcel Dekker, Inc., New York 355
- (2003) Clavicipitalean Fungi: Evolutionary Biology, Chemistry, Biocontrol, and Cultural Impacts , pp. 355
- Isaka, M.¹ Kittakoop, P.² Thebtaranonth, Y.³

3
- 0021042205
- Fukushima K., Arai T., and Mori Y. J. Antibiot. 36 (1983) 1606
- (1983) J. Antibiot. , vol.36 , pp. 1606
- Fukushima, K.¹ Arai, T.² Mori, Y.³

4
- 0021059178
- Fukushima K., Arai T., and Mori Y. J. Antibiot. 36 (1983) 1613
- (1983) J. Antibiot. , vol.36 , pp. 1613
- Fukushima, K.¹ Arai, T.² Mori, Y.³

5
- 0024378679
- Mikami Y., Yazawa K., and Fukushima K. Mycopathologia 108 (1989) 195
- (1989) Mycopathologia , vol.108 , pp. 195
- Mikami, Y.¹ Yazawa, K.² Fukushima, K.³

6
- 0028911084
- Frendenhagen A., Hug P., and Sauter H. J. Antibiot. 48 (1995) 199
- (1995) J. Antibiot. , vol.48 , pp. 199
- Frendenhagen, A.¹ Hug, P.² Sauter, H.³

7
- 20444478718
- Lang G., Blunt J.W., and Cummings N.J. J. Nat. Prod. 68 (2005) 810
- (2005) J. Nat. Prod. , vol.68 , pp. 810
- Lang, G.¹ Blunt, J.W.² Cummings, N.J.³

8
- 3242795745
- Kikuchi H., Miyagawa Y., Sahashi Y., Inatomi S., Haganuma A., Nakahata N., and Oshima Y. Tetrahedron Lett. 45 33 (2004) 6225
- (2004) Tetrahedron Lett. , vol.45 , Issue.33 , pp. 6225
- Kikuchi, H.¹ Miyagawa, Y.² Sahashi, Y.³ Inatomi, S.⁴ Haganuma, A.⁵ Nakahata, N.⁶ Oshima, Y.⁷

9
- 10044248459
- Kikuchi H., Miyagawa Y., and Nakamura K. Org. Lett. 6 (2004) 4531
- (2004) Org. Lett. , vol.6 , pp. 4531
- Kikuchi, H.¹ Miyagawa, Y.² Nakamura, K.³

10
- 0345871964
- Kikuchi H., Miyagawa Y., and Sahashi Y. J. Org. Chem. 69 (2004) 352
- (2004) J. Org. Chem. , vol.69 , pp. 352
- Kikuchi, H.¹ Miyagawa, Y.² Sahashi, Y.³

11
- 34248995226
- Isaka M., Palasam S., and Lapanun S. J. Nat. Prod. 70 (2007) 675
- (2007) J. Nat. Prod. , vol.70 , pp. 675
- Isaka, M.¹ Palasam, S.² Lapanun, S.³

12
- 33744481531
- Lang G., Mitova M.I., and Ellis G. J. Nat. Prod. 69 (2006) 621
- (2006) J. Nat. Prod. , vol.69 , pp. 621
- Lang, G.¹ Mitova, M.I.² Ellis, G.³

13
- 33645653117
- Van Heerbeek R., Kamer P.C.J., and Van Leeuwen P.N.M.W. Org. Biol. Chem. 4 (2006) 211
- (2006) Org. Biol. Chem. , vol.4 , pp. 211
- Van Heerbeek, R.¹ Kamer, P.C.J.² Van Leeuwen, P.N.M.W.³

14
- 62849119788
- Pentapeptide 3 (628 mg, 1 mmol) and O-prenyl-d-tryptophan fragment 6 (393 mg, 1.0 mmol) were dissolved in dichloromethane (10 mL) at 0 °C, after EDCI (320 g, 2.0 mmol) and DMAP (488 mg, 4 mmol) were added, the reaction was stirred at room temperature for 16 h. The reaction mixture successively washed with saturated NH4Cl solution (20 mL, saturated NaHCO3 solution (20 mL) and brine (20 mL, dried over anhydrous Na2SO4 and concentrated. The crude product was purified by silica gel chromatography, using 5% ethyl acetate-hexane as eluent, to afford the desired ester (2, 750 mg, 75, as clear oil. 1H NMR (500 MHz, CDCl3, δ ppm, 7.36-7.17 (m, 11H, 7.12 (d, 2H, J, 7.5 Hz, 6.91 (d, 2H, J, 6.9 Hz, 6.86 (d, 2H, J, 7.8 Hz, 5.48 (br s, 1H, 5.25 (br s, 1H, 4.76 (br s, 1H, 4.48 (d, 2H, J, 5.5 Hz, 4.40 (q, 2H, J, 7.1 Hz, 4.26-4.14 (m, 6H, 3.91 (d, 1H, J, 12.1 Hz, 3.70 (d, 1H, J, 12.3 Hz, 3.17-3.08 m, 4H
- + 1026.4692.

15
- 33845312505
- Carpino L.A., El-Faham A., and Minor C.A. J. Chem. Soc. Chem. Commun. (1994) 201
- (1994) J. Chem. Soc. Chem. Commun. , pp. 201
- Carpino, L.A.¹ El-Faham, A.² Minor, C.A.³

16
- 62849113063
- Precursor 2 (100 mg, 0.1 mmol) was treated with a solution of 0.1 mol/L TBAF in THF (5 mL) at 0 °C for 1 h. The reaction was allowed to warm to room temperature and stirred further for 4 h. The solvents were evaporated under reduced pressure to give the crude product, which was then dissolved in DMF (100 mL) and treated with HATU (142 mg, 0.4 mmol) at 25 °C for 30 min, and then DIPEA (0.11 mL, 0.6 mmol) was added to the reaction mixture. The reaction mixture was allowed to stir at this temperature for 48 h and DMF was then removed by distillation under vacuum at the temperature below 50 °C. The resulting crude product was purified by flash column chromatography on silica gel, using 2% MeOH in dichloromethane as eluent to afford the paecilodepsipeptide A (1, 54 mg, 72% over two steps) as a white solid. mp 138-140 °C;, α ]D25, 21.5 (c, 0.5, MeOH, lit, αD25, 22 (c, 0.15, MeOH, 1H NMR 500 MHz, DMS
- 9Na, 764.3271).

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.