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Volumn , Issue 20, 2006, Pages 3415-3418

Reagent-controlled regioselective [3,3]-sigmatropic rearrangement of N-trifluoroacetyl enehydroxylamine and its synthetic application

(5) Takeda, Norihiko a Miyata, Okiko a Kitamura, Maria a Kagehira, Shunsuke a Naito, Takeaki a

a KOBE PHARMACEUTICAL UNIVERSITY (Japan)

Author keywords

3,3 sigmatropic rearrangement; Benzofuran; Enehydroxylamine; Galanthamine; Lunarine

Indexed keywords

ALKALOID; BENZOFURAN DERIVATIVE; ETHER DERIVATIVE; HEXAHYDRODIBENZOFURAN; HYDROXYLAMINE; LUNARINE; N TRIFLUOROACETYLENEHYDROXYLAMINE; OXIME ETHER DERIVATIVE; REAGENT; SPERMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; ELECTRON; STEREOCHEMISTRY; SYNTHESIS;

EID: 33846513442 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2006-958431 Document Type: Article

Times cited : (6)

References (17)

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15
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- 1H NMR spectra while stereostructures of 6b and 6c have not been established.
- 1H NMR spectra while stereostructures of 6b and 6c have not been established.

16
- 33846549412
- The compounds 7a-c were obtained as a mixture of two diastereomers and found to be 4a, 9b-cis-configuration, but relative configuration at 4-position is not established
- The compounds 7a-c were obtained as a mixture of two diastereomers and found to be 4a, 9b-cis-configuration, but relative configuration at 4-position is not established.

17
- 33846554770
- Reaction of 5b with TFAA. To a solution of oxime ether 5b (47 mg, 0.18 mmol) in CH2Cl2 (1.8 mL) was added TFAA (0.050 mL, 0.36 mmol) under a nitrogen atmosphere at r.t. After being stirred at the same temperature for 4 h, the reaction mixture was concentrated at reduced pressure. Purification of the residue by medium-pressure column chromatography (n-hexane-EtOAc, 5:1) afforded ethyl 4a-(2,2,2-trifluoroacetamido)-1,2,3,4,4a, 9b-hexahydro-9b-dibenzofurancarboxylate (6b, 50 mg, 78, as colorless crystals, mp 39-41 °C (hexane, 1H NMR (500 MHz, CDCl3, δ, 8.70 (1 H, br s, 7.24 (1 H, br d, J, 8 Hz, 7.23 (1 H, br td, J, 8, 1 Hz, 6.98 (1 H, td, J, 8, 1 Hz, 6.95 (1 H, br d, J, 8 Hz, 4.37-4.27 (2 H, m, 2.87 (1 H, br dt, J, 15, 5 Hz, 2.39 (1 H, br dt, J, 15, 5Hz, 2.30 (1 H, br ddd, J, 15, 10, 5 Hz, 1.71-1.51 (5 H, m, 1.34 (3 H, t, J, 7 Hz, 13C NMR (125 MHz, CDCl3, δ, 172.7, 156.5, 156.1 q, C
- +]: 244.1098; found: 244.1107.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.