SCOPUS 정보 검색 플랫폼

Volumn , Issue 13, 2008, Pages 2028-2032

A concise diastereoselective approach to the left-hand side of batzelladine A

(6) Davies, Christopher D b Elliott, Mark C a Hill Cousins, Joseph a Khan, Misbah Ul A c Maqbool, Tahir a,c Wood, John L a

a CARDIFF UNIVERSITY (United Kingdom)

b ASTRAZENECA (United Kingdom)

c THE ISLAMIA UNIVERSITY OF BAHAWALPUR (Pakistan)

Author keywords

Alkaloids; Imines; Isothiocyanates; Multicomponent reactions; Stereoselectivity

Indexed keywords

ALKALOID DERIVATIVE; BATZELLADINE A;

ACYLATION; ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 49649104319 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1077969 Document Type: Article

Times cited : (19)

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32
- 49649115135
- Z)-Methyl [3-Methoxycarbonylamino)-3-phenyl-2-pyrrolidin-2-ylidene] propionate (16) Methyl TV-phenylmethylenecarbamate (15, 62 mg, 0.38 mmol) was added to a solution of (Z)-pyrrolidin-2-ylidene-acetic acid methyl ester (11, 54 mg, 0.38 mmol) in CH2Cl2 (5 mL, The resulting solution was stirred at r.t. overnight, concentrated in vacuo, and purified by flash column chromatography (eluent: hexane-EtOAc, 2:1; Rf= 0.4) to give the title compound (78 mg, 67, as a colourless oil. HRMS: m/z calcd for C16H21N2O4 [M, 305.1501. Found: 305.1515 [MH, 1HNMR (400 MHz, CDCl3, δ, 8.27 (1 H, br s, NH, 7.21-7.18 (4 H, m, J, 4.2 Hz, arom. CH, 7.14-7.08 (1 H, m, arom. CH, 5.91 (1 H, app. br d, J, 9.4 Hz,NH, 5.11(1 H, d, J, 10.0 Hz, CHPh, 3.65 (3 H, s, Me, 3.54-3.50 (2 H, m, CH2N, 3.42 (3 H, s, Me, 3.05 1 H, ddd
- +], 230 (100), 195 (43).

33
- 49649112996
- Z)-Ethyl 3-(Cyanoamino)-2-(pyrrolidin-2-ylidene)oct-anoate (18) Cyanamide (16 mg, 0.4 mmol) was added to a solution of hexanal (48 μL, 0.4 mmol) in dry CH2Cl2 (4 mL) under N2, and the resulting suspension was stirred at 25 °C for 30 min. A solution of (Z)-pyrrolidin-2-ylidene-acetic acid ethyl ester (17, 60 mg, 0.4 mmol) in CH2Cl2 (2 mL) was added, and the resulting mixture was stirred at 25 °C for 3 h. The solvent was then removed in vacuo to afford the title compound as a pale yellow gum (94 mg, 87% crude yield, 1H NMR (500 MHz, CDCl3, δ, 8.26 (1 H, br s, NH, 4.37 (1 H, br s, NHCN, 4.00-4.18 (2 H, m, CO2CH2, 3.75 (1 H, app. q, J, 7.4 Hz, CHNHCN, 3.50 (2 H, app. t, J, 7.0 Hz, CH2NH, 2.78 (1 H, ddd, J= 16.1, 9.1, 7.0 Hz, one of CH 2C=C, 2.58 1 H, ddd, J, 16.1, 9.2, 6.9 Hz, one of CH 2
- 2-alkyl).

34
- 49649103875
- Methyl (5S)-1,2,3,5,6,7-Hexahydro-3-(9-tert-butyl- diphenylsilyloxynonyl)-5-hydroxy-1-thioxopyrrolo[1,2-c]pyrimidine-4-carboxylate (25) Trimethylsilyl isothiocyanate (62 μL, 0.45 mmol) was added to a solution of aldehyde 26 (183 mg, 0.45 mmol) in dry CH2Cl 2 (3 mL) under N2, and the resulting brown solution was stirred for 30 min at 25 °C. A solution of alkylidene-pyrrolidine 24 (70 mg, 0.45 mmol) in CH2Cl2 (2 mL) was then added, and the reaction was stirred for 3 h. The reaction was quenched with ca. 0.1 M aq NaOH solution (20 ml) and the layers separated. The aqueous layer was washed with CH2Cl2 (3 x 25 mL, the combined organic layers dried with Na2SO4, and the solvent removed in vacuo. The resulting orange gum was purified by column chromatography (eluent: hexane-EtOAc, 2.5:1; Rf= 0.55) to give the title compound 79 mg, 29, as a
- 2).

35
- 0035902249
- Duron, S. G.; Gin, D. Y. Org. Lett. 2001, 3, 1551.
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- Duron, S.G.¹ Gin, D.Y.²

36
- 0025044033
- There is precedent for the deoxygenation of a secondary alcohol in the presence of an S-methylisothiourea, see ref. 19b. While we have been able to successfully S-methylate compound 25, the subsequent xanthate formation proved troublesome, and these studies are ongoing, (b) Buenger, G. S.; Nair, V. Synthesis 1990, 962.
- (a) There is precedent for the deoxygenation of a secondary alcohol in the presence of an S-methylisothiourea, see ref. 19b. While we have been able to successfully S-methylate compound 25, the subsequent xanthate formation proved troublesome, and these studies are ongoing, (b) Buenger, G. S.; Nair, V. Synthesis 1990, 962.

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