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Volumn , Issue 7, 2008, Pages 1050-1052

Regioselective synthesis of functionalized resorcins by cyclization of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with 3,3-dimethoxypentanoyl chloride

Author keywords

Arenes; Cyclizations; Regioselectivity; Silyl enol ethers

Indexed keywords

1,3 BIS(TRIMETHYLSILYLOXY) 1,3 BUTADIENE; 1,3 BUTADIENE; 3,3 DIMETHOXYPENTANOYL CHLORIDE; CHLORIDE; LEWIS ACID; RESORCINOL;

ARTICLE; CYCLIZATION; SYNTHESIS;

EID: 42949120197 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1072675 Document Type: Article

Times cited : (8)

References (25)

1
- 0034887171
- (a) Staunton, J.; Weissman, K. J. Nat. Prod. Rep. 2001, 18, 380.
- (2001) Nat. Prod. Rep , vol.18 , pp. 380
- Staunton, J.¹ Weissman, K.J.²

2
- 23644447866
- (b) Koskinen, A. M. P.; Karisalmi, K. Chem. Soc. Rev. 2005, 34, 677.
- (2005) Chem. Soc. Rev , vol.34 , pp. 677
- Koskinen, A.M.P.¹ Karisalmi, K.²

3
- 42949106177
- Römpp-Lexikon Naturstoffe; Fugmann, B., Ed.; Thieme: Stuttgart / New York, 1997.
- (c) Römpp-Lexikon Naturstoffe; Fugmann, B., Ed.; Thieme: Stuttgart / New York, 1997.

4
- 0013573627
- For a review, see: (a) Harris, T. M.; Harris, C. M. Tetrahedron 1977, 33, 2159. See also:
- For a review, see: (a) Harris, T. M.; Harris, C. M. Tetrahedron 1977, 33, 2159. See also:

5
- 3042822202
- (b) Murray, T. P.; Harris, T. M. J. Am. Chem. Soc. 1972, 94, 8253.
- (1972) J. Am. Chem. Soc , vol.94 , pp. 8253
- Murray, T.P.¹ Harris, T.M.²

6
- 0017130732
- (c) Harris, C. M.; Roberson, J. S.; Harris, T. M. J. Am. Chem. Soc. 1976, 98, 5380.
- (1976) J. Am. Chem. Soc , vol.98 , pp. 5380
- Harris, C.M.¹ Roberson, J.S.² Harris, T.M.³

7
- 0017398771
- (d) Harris, T. M.; Hay, J. V. J. Am. Chem. Soc. 1977, 99, 1631.
- (1977) J. Am. Chem. Soc , vol.99 , pp. 1631
- Harris, T.M.¹ Hay, J.V.²

8
- 0343265615
- (e) Hubbard, J. S.; Harris, T. M. Tetrahedron Lett. 1978, 47, 4601.
- (1978) Tetrahedron Lett , vol.47 , pp. 4601
- Hubbard, J.S.¹ Harris, T.M.²

9
- 0001506254
- (f) Sandifer, R. M.; Bhattacharya, A. K.; Harris, T. M. J. Org. Chem. 1981, 46, 2260.
- (1981) J. Org. Chem , vol.46 , pp. 2260
- Sandifer, R.M.¹ Bhattacharya, A.K.² Harris, T.M.³

10
- 0023777727
- (g) Gilbreath, S. G.; Harris, C. M.; Harris, T. M. J. Am. Chem. Soc. 1988, 110, 6172.
- (1988) J. Am. Chem. Soc , vol.110 , pp. 6172
- Gilbreath, S.G.¹ Harris, C.M.² Harris, T.M.³

11
- 0036200130
- For a review of 1,3-bissilyl enol ethers, see
- For a review of 1,3-bis(silyl enol ethers), see: Langer, P. Synthesis 2002, 441.
- (2002) Synthesis , pp. 441
- Langer, P.¹

12
- 33947178424
- For a review of formal [3+3] cyclizations of 1,3-bis(silyl enol ethers), see: Feist, H.; Langer, P. Synthesis 2007, 327.
- For a review of formal [3+3] cyclizations of 1,3-bis(silyl enol ethers), see: Feist, H.; Langer, P. Synthesis 2007, 327.

13
- 0004780864
- Chan, T.-H.; Brownbridge, P. J. Chem. Soc., Chem. Commun. 1979, 578.
- (1979) J. Chem. Soc., Chem. Commun , pp. 578
- Chan, T.-H.¹ Brownbridge, P.²

14
- 33845280231
- (a) Chan, T.-H.; Stössel, D. J. Org. Chem. 1988, 53, 4901.
- (1988) J. Org. Chem , vol.53 , pp. 4901
- Chan, T.-H.¹ Stössel, D.²

15
- 0000440808
- (b) Chan, T.-H.; Stössel, D. J. Org. Chem. 1986, 51, 2423.
- (1986) J. Org. Chem , vol.51 , pp. 2423
- Chan, T.-H.¹ Stössel, D.²

16
- 0035901649
- Langer, P.; Krummel, T. Chem. Eur. J. 2001, 7, 1720.
- (2001) Chem. Eur. J , vol.7 , pp. 1720
- Langer, P.¹ Krummel, T.²

17
- 33947198869
- Rahn, T.; Nguyen, V. T. H.; Dang, T. H. T.; Ahmed, Z.; Lalk, M.; Fischer, C.; Spannenberg, A.; Langer, P. J. Org. Chem. 2007, 72, 1957.
- (2007) J. Org. Chem , vol.72 , pp. 1957
- Rahn, T.¹ Nguyen, V.T.H.² Dang, T.H.T.³ Ahmed, Z.⁴ Lalk, M.⁵ Fischer, C.⁶ Spannenberg, A.⁷ Langer, P.⁸

18
- 33846471698
- For a review of cyclizations of silyl enol ethers with oxalyl chloride, see
- For a review of cyclizations of silyl enol ethers with oxalyl chloride, see: Langer, P. Synlett 2006, 3369.
- (2006) Synlett , pp. 3369
- Langer, P.¹

19
- 33646007359
- Albrecht, U.; Nguyen, V. T. H.; Langer, P. Synthesis 2006, 1111.
- (2006) Synthesis , pp. 1111
- Albrecht, U.¹ Nguyen, V.T.H.² Langer, P.³

20
- 27644513126
- Reim, S.; Nguyen, V. T. H.; Albrecht, U.; Langer, P. Tetrahedron Lett. 2005, 46, 8423.
- (2005) Tetrahedron Lett , vol.46 , pp. 8423
- Reim, S.¹ Nguyen, V.T.H.² Albrecht, U.³ Langer, P.⁴

21
- 42949141686
- Some years ago, an isolated example of the cyclization of a protected β-keto ester was reported, see ref. 12b. In the case of 2, this reaction failed to give the desired product (formation of a complex mixture). An isolated reaction of a 1,3-dioxolan-protected β-keto acid chloride was also reported by Chan and Chaly. However, in our hands, the use of the dioxolan group proved to be disadvantageous in order to isolate the desired product in pure form.
- (a) Some years ago, an isolated example of the cyclization of a protected β-keto ester was reported, see ref. 12b. In the case of 2, this reaction failed to give the desired product (formation of a complex mixture). An isolated reaction of a 1,3-dioxolan-protected β-keto acid chloride was also reported by Chan and Chaly. However, in our hands, the use of the dioxolan group proved to be disadvantageous in order to isolate the desired product in pure form.

22
- 0019974594
- (b) Chan, T. H.; Chaly, T. Tetrahedron Lett. 1982, 23, 2935.
- (1982) Tetrahedron Lett , vol.23 , pp. 2935
- Chan, T.H.¹ Chaly, T.²

23
- 42949125995
- Typical Procedure for the Synthesis of 6a-1 To a CH 2Cl2 solution (8 mL) of 1,3-bis(trimethylsilyloxy)-1- methoxy-1,3-butadiene (5a, 860 mg, 3.32 mmol) and of 4 (660 mg, 3.65 mmol) was dropwise added TMSOTf (0.3 mL, 1.66 mmol, 0.5 equiv) at -78°C. The reaction mixture was allowed to warm to 20°C during 6-12 h. After stirring for additional 2-6 h at 20°C, HCl (10, 25 mL) was added. The organic and the aqueous layers were separated and the latter was extracted with CH2Cl2 (3 x 20 mL, The combined organic layers were dried (NaSO4, filtered, and the filtrate was concentrated in vacuo. The residue was purified by chromatography (SiO2, heptanes-EtOAc) to give 6a as yellow solid (280 mg, 43, 1H NMR (300 MHz, CDCl3, δ, 1.13 (t, 3 H, J, 7.6 Hz, CH3, 2.48 (q, 2 H, J, 7.5 Hz. CH2, 3.99 s, 3 H, OCH 3, 6.28
- 4 (196.07): C, 61.22; H, 6.16. Found: C, 61.32; H, 6.11.

24
- 42949136070
- Typical Procedure for the Synthesis of 7a-i To a CH 2Cl2 solution (5 mL) of 1,3-bis(trimethylsilyloxy)-1- methoxy-1,3-butadiene (500 mg, 1.91 mmol) and of 4 (385 mg, 2.11 mmol) was added dropwise TiCl4 (0.21 mL, 1.91 mmol) at -78°C. The reaction mixture was allowed to warm to 20°C during 6-12 h. After stirring for additional 2-6 h at 20°C, a sat. aq solution of NaHCO3 (20 mL) was added. The organic and the aqueous layers were separated and the latter was extracted with Et2O (3 x 25 mL, The combined organic layers were dried (NaSO4, filtered and the filtrate was concentrated in vacuo. The residue was purified by chromatography (SiO2, heptane-EtOAc) to give 7a as a yellow solid (230 mg, 61, 1H NMR (300 MHz, CDCl3, δ, 1.30 (t, 3 H, J, 7.5 Hz, CH3, 3.28 (q, 2 H, J, 7.5 Hz, CH2, 4.01 s, 3 H, OCH 3
- +: 196.072572; found: 196.07301.

25
- 33847086576
- Murata, S.; Suzuki, M.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 3248.
- (1980) J. Am. Chem. Soc , vol.102 , pp. 3248
- Murata, S.¹ Suzuki, M.² Noyori, R.³

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