SCOPUS 정보 검색 플랫폼

Volumn , Issue 4, 2008, Pages 575-577

Synthesis of (±)-smenochromene D (likonide B) using a regioselective claisen rearrangement

Author keywords

ansa macrocycles; Chromenes; Mitsunobu reaction; Natural products; Rearrangements

Indexed keywords

CHROMENE DERIVATIVE; ETHER DERIVATIVE; QUINONE DERIVATIVE; SMENOCHROMENE D; UNCLASSIFIED DRUG;

ARTICLE; CLAISEN REARRANGEMENT; CYCLIZATION; MICROWAVE RADIATION; MITSUNOBU REACTION; MOLECULAR INTERACTION; SYNTHESIS;

EID: 40949101412 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1032090 Document Type: Article

Times cited : (10)

References (22)

1
- 0003868021
- 2nd ed, Academic Press: London
- Thomson, R. H. Naturally Occurring Quinones, 2nd ed.; Academic Press: London, 1971.
- (1971) Naturally Occurring Quinones
- Thomson, R.H.¹

2
- 0003868021
- 3rd ed, Chapman and Hall: London
- Thomson, R. H. Naturally Occurring Quinones III: Recent Advances, 3rd ed.; Chapman and Hall: London, 1987.
- (1987) Naturally Occurring Quinones III: Recent Advances
- Thomson, R.H.¹

3
- 0003868021
- 4th ed, Blackie: London
- Thomson, R. H. Naturally Occurring Quinones IV: Recent Advances, 4th ed.; Blackie: London, 1997.
- (1997) Naturally Occurring Quinones IV: Recent Advances
- Thomson, R.H.¹

4
- 8744239167
- Rudi, A.; Benayahu, Y.; Kashman, Y. Org. Lett. 2004, 6, 4013.
- (2004) Org. Lett , vol.6 , pp. 4013
- Rudi, A.¹ Benayahu, Y.² Kashman, Y.³

5
- 0000744569
- Venkateswarlu, Y.; Faulkner, D. J.; Steiner, J. L. R.; Corcoran, E.; Clardy, J. J. Org. Chem. 1991, 56, 6271.
- (1991) J. Org. Chem , vol.56 , pp. 6271
- Venkateswarlu, Y.¹ Faulkner, D.J.² Steiner, J.L.R.³ Corcoran, E.⁴ Clardy, J.⁵

6
- 15444380491
- Olson, B. S.; Trauner, D. Synlett 2005, 700.
- (2005) Synlett , pp. 700
- Olson, B.S.¹ Trauner, D.²

7
- 34249314424
- Rosa, C. P.; Kienzler, M. A.; Olson, B. S.; Liang, G.; Trauner, D. Tetrahedron 2007, 63, 6529.
- (2007) Tetrahedron , vol.63 , pp. 6529
- Rosa, C.P.¹ Kienzler, M.A.² Olson, B.S.³ Liang, G.⁴ Trauner, D.⁵

8
- 0033576690
- Stahl, P.; Waldmann, H. Angew. Chem. Int. Ed. 1999, 38, 3710.
- (1999) Angew. Chem. Int. Ed , vol.38 , pp. 3710
- Stahl, P.¹ Waldmann, H.²

9
- 16644395180
- Aoki, S.; Kong, D.; Matsui, K.; Rachmat, R.; Kobayashi, M. Chem. Pharm. Bull. 2004, 52, 935.
- (2004) Chem. Pharm. Bull , vol.52 , pp. 935
- Aoki, S.¹ Kong, D.² Matsui, K.³ Rachmat, R.⁴ Kobayashi, M.⁵

10
- 34547137678
- Takahashi, Y.; Kubota, T.; Fromont, J.; Kobayashi, J. Tetrahedron 2007, 63, 8770.
- (2007) Tetrahedron , vol.63 , pp. 8770
- Takahashi, Y.¹ Kubota, T.² Fromont, J.³ Kobayashi, J.⁴

11
- 0024806911
- McMurry, J. E.; Dushin, R. G. J. Chem. Soc. 1989, 111, 8928.
- (1989) J. Chem. Soc , vol.111 , pp. 8928
- McMurry, J.E.¹ Dushin, R.G.²

12
- 33847089541
- Umbreit, M. A.; Sharpless, K. B. J. Am. Chem. Soc. 1977, 99, 5526.
- (1977) J. Am. Chem. Soc , vol.99 , pp. 5526
- Umbreit, M.A.¹ Sharpless, K.B.²

13
- 2442630439
- Fischer, J.; Reynolds, A. J.; Sharp, L. A.; Sherburn, M. S. Org. Lett. 2004, 6, 1345.
- (2004) Org. Lett , vol.6 , pp. 1345
- Fischer, J.¹ Reynolds, A.J.² Sharp, L.A.³ Sherburn, M.S.⁴

14
- 0027940323
- Godfrey, J. D.; Mueller, R. H.; Sedergran, T. C.; Soundararajan, N.; Colandrea, V. J. Tetrahedron Lett. 1994, 35, 6405.
- (1994) Tetrahedron Lett , vol.35 , pp. 6405
- Godfrey, J.D.¹ Mueller, R.H.² Sedergran, T.C.³ Soundararajan, N.⁴ Colandrea, V.J.⁵

15
- 0033550229
- For related Claisen rearrangements, see ref. 16 and the following: Kahn, P. H.; Cossy, J. Tetrahedron Lett. 1999, 40, 8113.
- For related Claisen rearrangements, see ref. 16 and the following: Kahn, P. H.; Cossy, J. Tetrahedron Lett. 1999, 40, 8113.

16
- 4344571595
- Yamaguchi, S.; Maekawa, M.; Murayama, Y.; Miyazawa, M.; Hirai, Y. Tetrahedron Lett. 2004, 45, 6971.
- (2004) Tetrahedron Lett , vol.45 , pp. 6971
- Yamaguchi, S.¹ Maekawa, M.² Murayama, Y.³ Miyazawa, M.⁴ Hirai, Y.⁵

17
- 0035808879
- For a discussion of regioselectivity in rearrangements of aryl propargyl ethers, see
- For a discussion of regioselectivity in rearrangements of aryl propargyl ethers, see: Yamaguchi, S.; Ishibashi, M.; Akasaka, K.; Yokoyama, H.; Miyazawa, M.; Hirai, Y. Tetrahedron Lett. 2001, 42, 1091.
- (2001) Tetrahedron Lett , vol.42 , pp. 1091
- Yamaguchi, S.¹ Ishibashi, M.² Akasaka, K.³ Yokoyama, H.⁴ Miyazawa, M.⁵ Hirai, Y.⁶

18
- 0002816437
- For an earlier example of a microwave-assisted Claisen rearrangement of an aryl propargyl ether, see
- For an earlier example of a microwave-assisted Claisen rearrangement of an aryl propargyl ether, see: Moghaddam, F. M.; Sharifi, A.; Saidi, M. R. J. Chem. Res., Synop. 1996, 338.
- (1996) Chem. Res., Synop , pp. 338
- Moghaddam, F.M.¹ Sharifi, A.² Saidi, M.R.J.³

19
- 2442466846
- Ritter, T.; Stanek, K.; Larrosa, I.; Carreira, E. M. Org. Lett. 2004, 6, 1513.
- (2004) Org. Lett , vol.6 , pp. 1513
- Ritter, T.¹ Stanek, K.² Larrosa, I.³ Carreira, E.M.⁴

20
- 40949100998
- 6-Hydroxy-2, 3E,7E, 9-tert-butyldimethylsilyloxy-4,8-dimethylnona-3,7-dienyl, 7-methoxy-2-methyl-2H-chromene (7b, A solution of the propargyl aryl ether (98 mg, 0.21 mmol) in N,N-diethylaniline (3.5 mL) in a sealed tube was heated at 140 °C for 40 min at 300 W in a CEM Discover™ microwave reactor. The reaction mixture was evaporated and the resulting oil was purified by flash chromatography on silica gel, eluting with light PE-Et2O (8:2, to give the title compound (85 mg, 87, as a orange-yellow oil. IR (CHCl3, 3630, 3553, 2929, 2856, 1628, 1583, 1501, 1458, 1360, 1290, 1124 cm-1. 1H NMR (400 MHz, CDCl3, δ, 6.56 (s, 1 H, H-5, 6.41 (s, 1 H, H-8, 6.27 (d, J, 9.8 Hz, 1 H, H-4, 5.47 (d, J, 9.8 Hz, 1 H, H-3, 5.38 (m, 1 H, CH=CMe, 5.19 (s, 1 H, OH, 5.13-5.16 (m, 1 H, CH=CMe, 4.02 (s, 2 H, OCH2, 3.86 s
- 4Si: 495.2901; found: 495.2918.

21
- 40949107398
- ±)-Smenochromene D, ±)-Likonide B](2, Into a stirring 8 mM solution of 6-hydroxy-2, 3E,7E)-9-hydroxy-4,8- dimethylnona-3,7-dienyl]-7-methoxy-2-methyl-2H-chromene (8; 50 mg, 0.14 mmol) and dipiperidinyl azodicarboxylate (105 mg, 0.42 mmol) in anhyd toluene (17.4 mL) was bubbled argon for 10 min, while cooling the solution to 0 °C A first batch (40 μL) of tributylphosphine (140 μL, 0.55 mmol) was added dropwise and the reaction mixture was stirred for 20 min at 0 °C followed by the addition of a second batch of tributylphosphine (100 μL, The reaction mixture was then allowed to reach r.t. and was stirred for 24 h. A second batch of dipiperidinyl azodicarboxylate was added at 0 °C, tributylphosphine was added over 1 h and the whole was stirred for 8 h at r.t. H2O was added to the mixture and the aqueous phase was extracted into EtOAc 2 x, The organic layer was reduced in vacuo, the crude product was ta
- 3: 363.1931; found: 363.1919. The cyclic dimer 9 (13 mg, 13%) was also isolated.

22
- 40949100058
- A similarly modest yield in the macrocyclisation step was also observed in the previous synthesis of smenochromene D ref. 6
- A similarly modest yield in the macrocyclisation step was also observed in the previous synthesis of smenochromene D (ref. 6).

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.