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Volumn , Issue 5, 2007, Pages 800-802

New access to a tricyclo[3.2.1.02,7]oct-3-ene structure

Author keywords

1,4 elimination; Diels Alder; Electrocyclic reaction; Polycycles; Stereoselective synthesis

Indexed keywords

CAFESTOL; CARBONIC ACID; OCTANE; TRICYCLO[3.2.1.0 2,7]OCT 3 ENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CRYSTAL STRUCTURE; DIELS ALDER REACTION; SYNTHESIS; X RAY DIFFRACTION;

EID: 33947722645 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-970761 Document Type: Article

Times cited : (5)

References (19)

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15
- 33947714552
- Methyl 3-Phenylcyclobut-2-enyl Carbonate (5, To a solution of 3-phenylcyclobutenone (3, 2.1 g, 14.5 mmol) and CeCl3·7H 2O (5.6 g, 22.7 mmol) in MeOH (50 mL) at r.t. was slowly added NaBH4 (580 mg, 15 mmol) over 15 min. The reaction mixture was stirred at that temperature for 5 min, hydrolyzed with brine (50 mL) and extracted with Et2O (3 x 50 mL, The organic layer was dried over MgSO4 and evaporated to give a residue (2.1 g) which was dissolved in CH 2Cl2 (150 mL) in the presence of Et3N (8 mL, 57 mmol) and 4-dimethylamino pyridine (1 g, 8 mmol, Then, ClCO2Me (4.7 mL, 60 mmol) was slowly added and the reaction mixture was stirred for 75 min at r.t. After dilution in CH2Cl2 (50 mL, it was hydrolyzed with brine (100 mL) and extracted with Et2O 3 x 100 mL, The organic layer was dried over MgSO4, evaporated and the residue was pu
- 2H].

16
- 33947712439
- Compounds 6: The carbonate 5 (300 mg, 1.5 mmol) in DMSO (1 mL) was heated at DMSO reflux for 1.5 h under argon. The crude reaction mixture was diluted with brine (15 mL) and extracted with EtOAc (3 x 10 mL, The organic layer was dried over MgSO4, evaporated and the residue was purified by flash chromatography (CH2Cl2-pentane, 1:2) to give the compound 6 as a white solid (84 mg, 33, 1H NMR (300 MHz, CDCl3, δ, 7.50-7.20 (m, 10 H, arom, 6.59 (dd, J, 6.2, 2.3 Hz, H3, 5.26 (dd, J, 4.7, 2.3 Hz, 1 H, H 6, 3.71 (t, J, 3.9 Hz, 1 H, H5, 3.69 (s, 3 H, H10, 2.35 (dd, J, 6.8, 2.4 Hz, 1 H, H7, 2.23 (dd, J, 8.0, 6.2 Hz, 1 H, H2, 2.18 (dd, J, 11.7, 5.1 Hz, 1 H, H8′, 1.57 (d, J, 11.7 Hz, 1 H, H 8) ppm. 13CNMR75 MHz, CDCl3, δ, 155
- 3: C, 79.50; H, 6.06. Found: C, 79.50; H, 6.31.

17
- 33947722894
- The carbonate 5 (368 mg, 1.8 mmol) was heated at 140°C (neat) for 30 min. The residue was purified by flash chromatography (pentane-Et 2O, 95:5, followed by pentane-Et2O, 80:20) to afford successively the tricyclic compound 6 as a white solid (62 mg, 21, a mixture of the diastereomers 8 (69 mg, 19, and diene 7 (10 mg, 5, Diastereomers 8: 1H NMR (300 MHz, CDCl3, δ, 7.50-7.20 (m, 20 H, Ph, 6.95 (d, J, 12.6 Hz, 1 H, CH trans, 6.91 (d, J, 12.7 Hz, 1 H, CHtrans, 6.32 (br d, J, 5.1 Hz, 1 H, CH, 6.29 (dt, J, 4.3, 1.6 Hz, 1 H, CH, 5.73 (d, J, 12.6 Hz, 1 H, CHtrans, 5.65 (d, J, 4.3 Hz, 1 H, CHO, 5.63 (d, J, 12.7 Hz, 1 H, CHtrans, 5.51 (d, J, 5.1 Hz, 1 H, CHO, 3.82 (s, 3 H, OMe, 3.81 (s, 3 H, OMe, 3.77 (s, 3 H, OMe, 3.55 (s, 3 H, OMe, 2.70-2.40 m, 4 H, CH2, 2.40-2.10
- 2].

18
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19
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- Hill, R. K.; Bock, M. G. J. Am. Chem. Soc. 1978, 100, 637.
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- Hill, R.K.¹ Bock, M.G.²

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