SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 14, 2008, Pages 2164-2168

Concise synthesis of key 3-polyenoyl-5-methylenefuran-2,4-dione putative intermediates in quartromicin biosynthesis

(2) Montgomery, Laura J a,b Challis, Gregory L a

a UNIVERSITY OF WARWICK (United Kingdom)

b CXR Biosciences Ltd (United Kingdom)

Author keywords

Acylations; Antibiotics; Biosynthesis; Quartromicins; Spirotetronates

Indexed keywords

3 LITHIO 4 METHOXY 5 METHYLENE 5H FURAN 2 ONE; 3 POLYENOYL 5 METHYLENEFURAN 2,4 DIONE; ANTIBIOTIC AGENT; FURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; CYCLOADDITION; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 51149086592 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1078247 Document Type: Article

Times cited : (5)

References (33)

1
- 0026577158
- Tsunakawa, M.; Tenmyo, O.; Tomita, K.; Naruse, N.; Kotake, C.; Miyaki, T.; Konishi, M.; Oki, T. J. Antibiot. 1992, 45, 180.
- (1992) J. Antibiot , vol.45 , pp. 180
- Tsunakawa, M.¹ Tenmyo, O.² Tomita, K.³ Naruse, N.⁴ Kotake, C.⁵ Miyaki, T.⁶ Konishi, M.⁷ Oki, T.⁸

2
- 84980128776
- (a) Keller-Schierlein, W.; Muntwyler, R.; Pache, W.; Zaehner, H. Helv. Chim. Acta 1969, 52, 127.
- (1969) Helv. Chim. Acta , vol.52 , pp. 127
- Keller-Schierlein, W.¹ Muntwyler, R.² Pache, W.³ Zaehner, H.⁴

3
- 0015277592
- (b) Muntwyler, R.; Keller-Schierlein, W. Helv. Chim. Acta 1972, 55, 2071.
- (1972) Helv. Chim. Acta , vol.55 , pp. 2071
- Muntwyler, R.¹ Keller-Schierlein, W.²

4
- 0015275364
- (c) Brufani, M.; Cerrini, S.; Fedeli, W.; Mazza, F.; Muntwyler, R. Helv. Chim. Acta 1972, 55, 2094.
- (1972) Helv. Chim. Acta , vol.55 , pp. 2094
- Brufani, M.¹ Cerrini, S.² Fedeli, W.³ Mazza, F.⁴ Muntwyler, R.⁵

5
- 0019782467
- (a) Mallams, A. K.; Puar, M. S.; Rossman, R. R. J. Am. Chem. Soc. 1981, 103, 3938.
- (1981) J. Am. Chem. Soc , vol.103 , pp. 3938
- Mallams, A.K.¹ Puar, M.S.² Rossman, R.R.³

6
- 0019774238
- (b) Mallams, A. K.; Puar, M. S.; Rossman, R. R.; McPhail, A. T.; Macfarlane, R. D. J. Am. Chem. Soc. 1981, 103, 3940.
- (1981) J. Am. Chem. Soc , vol.103 , pp. 3940
- Mallams, A.K.¹ Puar, M.S.² Rossman, R.R.³ McPhail, A.T.⁴ Macfarlane, R.D.⁵

7
- 0019799763
- (c) Waitz, J. A.; Horan, A. C.; Kalyanpur, M.; Lee, B. K.; Loebenberg, D.; Marquez, J. A.; Miller, G.; Patel, M. G. J. Antibiot. 1981, 34, 1101.
- (1981) J. Antibiot , vol.34 , pp. 1101
- Waitz, J.A.¹ Horan, A.C.² Kalyanpur, M.³ Lee, B.K.⁴ Loebenberg, D.⁵ Marquez, J.A.⁶ Miller, G.⁷ Patel, M.G.⁸

8
- 37049110428
- (d) Mallams, A. K.; Puar, M. S.; Rossman, R. R.; McPhail, A. T.; Macfarlane, R. D.; Stephens, R. L. J. Chem. Soc., Perkin Trans. 1 1983, 1497.
- (1983) J. Chem. Soc., Perkin Trans. 1 , pp. 1497
- Mallams, A.K.¹ Puar, M.S.² Rossman, R.R.³ McPhail, A.T.⁴ Macfarlane, R.D.⁵ Stephens, R.L.⁶

9
- 0026325940
- Kusumi, T.; Ichikawa, A.; Kakisawa, H.; Tsunakawa, M.; Konishi, M.; Oki, T. J. Am. Chem. Soc. 1991, 113, 8947.
- (1991) J. Am. Chem. Soc , vol.113 , pp. 8947
- Kusumi, T.¹ Ichikawa, A.² Kakisawa, H.³ Tsunakawa, M.⁴ Konishi, M.⁵ Oki, T.⁶

10
- 0037007723
- (a) Roush, W. R.; Barda, D. A. Org. Lett. 2002, 4, 1539.
- (2002) Org. Lett , vol.4 , pp. 1539
- Roush, W.R.¹ Barda, D.A.²

11
- 0037025962
- (b) Roush, W. R.; Barda, D. A.; Limberakis, C.; Kunz, R. K. Tetrahedron 2002, 58, 6433.
- (2002) Tetrahedron , vol.58 , pp. 6433
- Roush, W.R.¹ Barda, D.A.² Limberakis, C.³ Kunz, R.K.⁴

12
- 0037007705
- (a) Roush, W. R.; Limberakis, C.; Kunz, R. K.; Barda, D. A. Org. Lett. 2002, 4, 1543.
- (2002) Org. Lett , vol.4 , pp. 1543
- Roush, W.R.¹ Limberakis, C.² Kunz, R.K.³ Barda, D.A.⁴

13
- 25444461699
- (b) Bedel, O.; Franxais, A.; Haudrechy, Y. Synlett 2005, 2313.
- (2005) Synlett , pp. 2313
- Bedel, O.¹ Franxais, A.² Haudrechy, Y.³

14
- 33750460591
- (c) Trullinger, T. K.; Qi, J.; Roush, W. R. J. Org. Chem. 2006, 71, 6915.
- (2006) J. Org. Chem , vol.71 , pp. 6915
- Trullinger, T.K.¹ Qi, J.² Roush, W.R.³

15
- 33745184421
- Jia, X.-Y.; Tian, Z.-H.; Shao, L.; Qu, X.-D.; Zhao, Q.-F.; Tang, J.; Tang, G.-L.; Liu, W. Chem. Biol. 2006, 13, 575.
- (2006) Chem. Biol , vol.13 , pp. 575
- Jia, X.-Y.¹ Tian, Z.-H.² Shao, L.³ Qu, X.-D.⁴ Zhao, Q.-F.⁵ Tang, J.⁶ Tang, G.-L.⁷ Liu, W.⁸

16
- 36749055680
- Zhang, H.; White-Phillip, J. A.; Melancon, C. E. III.; Kwon, H.-J.; Yu, W.-L.; Liu, H.-W. J Am. Chem. Soc. 2007, 129, 14670.
- (2007) J Am. Chem. Soc , vol.129 , pp. 14670
- Zhang, H.¹ White-Phillip, J.A.² Melancon III, C.E.³ Kwon, H.-J.⁴ Yu, W.-L.⁵ Liu, H.-W.⁶

17
- 38149064397
- (a) Sun, Y.; Hong, H.; Gillies, F.; Spencer, J. B.; Leadlay, P. F. ChemBioChem. 2008, 9, 150.
- (2008) ChemBioChem , vol.9 , pp. 150
- Sun, Y.¹ Hong, H.² Gillies, F.³ Spencer, J.B.⁴ Leadlay, P.F.⁵

18
- 46649112563
- (b) Demydchuk, Y.; Sun, Y.; Hong, H.; Staunton, J.; Spencer, J. B.; Leadlay, P. F. ChemBioChem. 2008, 9, 1136.
- (2008) ChemBioChem , vol.9 , pp. 1136
- Demydchuk, Y.¹ Sun, Y.² Hong, H.³ Staunton, J.⁴ Spencer, J.B.⁵ Leadlay, P.F.⁶

19
- 3042745794
- Oikawa, H.; Tokiwano, T. Nat. Prod. Rep. 2004, 21, 321.
- (2004) Nat. Prod. Rep , vol.21 , pp. 321
- Oikawa, H.¹ Tokiwano, T.²

20
- 0001080932
- For recent examples, see: a
- For recent examples, see: (a) Dixon, D. J.; Ley, S. V.; Gracza, T.; Szolcsanyi, P. J. Chem. Soc., Perkin Trans. 1 1999, 839.
- (1999) J. Chem. Soc., Perkin Trans. 1 , pp. 839
- Dixon, D.J.¹ Ley, S.V.² Gracza, T.³ Szolcsanyi, P.⁴

21
- 0001601710
- (b) Dixon, D. J.; Ley, S. V.; Longbottom, D. A. J. Chem. Soc., Perkin Trans. 1 1999, 2231.
- (1999) J. Chem. Soc., Perkin Trans. 1 , pp. 2231
- Dixon, D.J.¹ Ley, S.V.² Longbottom, D.A.³

22
- 0035959985
- (c) Sodeoka, M.; Sampe, R.; Kojima, S.; Baba, Y.; Usui, T.; Ueda, K.; Osada, H. J. Med. Chem. 2001, 44, 3216.
- (2001) J. Med. Chem , vol.44 , pp. 3216
- Sodeoka, M.¹ Sampe, R.² Kojima, S.³ Baba, Y.⁴ Usui, T.⁵ Ueda, K.⁶ Osada, H.⁷

23
- 0013561667
- For examples, see: a
- For examples, see: (a) Takeda, K.; Yano, S.; Yoshii, E. Tetrahedron Lett. 1988, 29, 6951.
- (1988) Tetrahedron Lett , vol.29 , pp. 6951
- Takeda, K.¹ Yano, S.² Yoshii, E.³

24
- 0025902351
- (b) Takeda, K.; Kawanishi, E.; Nakamura, H.; Yoshii, E. Tetrahedron Lett. 1991, 32, 4925.
- (1991) Tetrahedron Lett , vol.32 , pp. 4925
- Takeda, K.¹ Kawanishi, E.² Nakamura, H.³ Yoshii, E.⁴

25
- 27644479911
- (c) Snider, B. B.; Zou, Y. Org. Lett. 2005, 7, 4939.
- (2005) Org. Lett , vol.7 , pp. 4939
- Snider, B.B.¹ Zou, Y.²

26
- 27144521210
- (d) Zapf, C. W.; Harrison, B. A.; Drahl, C.; Sorensen, E. J. Angew. Chem. Int. Ed. 2005, 44, 6533.
- (2005) Angew. Chem. Int. Ed , vol.44 , pp. 6533
- Zapf, C.W.¹ Harrison, B.A.² Drahl, C.³ Sorensen, E.J.⁴

27
- 33646471096
- (e) Couladouros, E. A.; Bouzas, E. A.; Magos, A. D. Tetrahedron 2006, 62, 5272.
- (2006) Tetrahedron , vol.62 , pp. 5272
- Couladouros, E.A.¹ Bouzas, E.A.² Magos, A.D.³

28
- 33846195899
- (f) Nicolaou, K. C.; Harrison, S. T. J. Am. Chem. Soc. 2007, 129, 429.
- (2007) J. Am. Chem. Soc , vol.129 , pp. 429
- Nicolaou, K.C.¹ Harrison, S.T.²

29
- 0023641133
- (a) Takeda, K.; Yano, S.; Sato, M.; Yoshii, E. J. Org. Chem. 1987, 52, 4135.
- (1987) J. Org. Chem , vol.52 , pp. 4135
- Takeda, K.¹ Yano, S.² Sato, M.³ Yoshii, E.⁴

30
- 0034676689
- (b) Paintner, F. F.; Bauschke, G.; Kestel, M. Tetrahedron Lett. 2000, 41, 9977.
- (2000) Tetrahedron Lett , vol.41 , pp. 9977
- Paintner, F.F.¹ Bauschke, G.² Kestel, M.³

31
- 37049072174
- Pelter, A.; Al-Bayati, R. I. H.; Ayoub, M. T.; Lewis, W.; Pardasani, P.; Hansel, R. J. Chem. Soc., Perkin Trans. 1 1987, 717.
- (1987) J. Chem. Soc., Perkin Trans. 1 , pp. 717
- Pelter, A.¹ Al-Bayati, R.I.H.² Ayoub, M.T.³ Lewis, W.⁴ Pardasani, P.⁵ Hansel, R.⁶

32
- 0032575183
- Wei, X.; Taylor, R. J. K. Tetrahedron Lett. 1998, 39, 3815.
- (1998) Tetrahedron Lett , vol.39 , pp. 3815
- Wei, X.¹ Taylor, R.J.K.²

33
- 51149087726
- General Procedure for the Acylation of Compounds 18 and 28: To a stirred solution of 2,2,6,6-tetramethylpiperidine (TMP, 0.84 mL, 5.00 mmol) in THF (5.50 mL) at -78°C under argon was added n-BuLi (1.60 M in hexanes, 3.70 mL, 5.92 mmol) dropwise. After 15 min the solution was warmed to r.t. and stirred for a further 30 min to give a 0.5 M solution of LTMP. To a stirred solution of 18 or 28 (1.4 mmol) in THF (20 mL) at -78°C under argon was added a solution of LTMP (0.5 M in THF, 4.40 mL, 2.20 mmol) dropwise. After stirring for 1 h, a solution of ester (0.70 mmol) in THF (2 mL) was added dropwise. The reaction mixture was stirred at -78°C for 24 h and quenched with sat. citric acid (20 mL, The organic layer was separated, and the aqueous layer was extracted with CH2Cl2 5 x 50 mL, The combined organic layers were dried with MgSO4 and the solvent was removed in vacuo. Purification and Characterization of Compoun
- +: 351.1561; found: 351.1573.

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