SCOPUS 정보 검색 플랫폼

Volumn , Issue 18, 2008, Pages 2781-2784

Tandem aza-Michael-condensation-Aldol cyclization reaction: Approach to the construction of DE synthon of (±)-camptothecin

(3) Chavan, Subhash P a Dhawane, Abasaheb N a Kalkote, Uttam R a

a NATIONAL CHEMICAL LABORATORY (India)

Author keywords

Aldol cyclizations; Alkaloids; Antitumor; Natural products; Reformatsky reaction

Indexed keywords

CAMPTOTHECIN; CAMPTOTHECIN DERIVATIVE; CHLORIDE; PYRIDONE DERIVATIVE;

ALDOL REACTION; ARTICLE; CYCLIZATION; DRUG STRUCTURE; MICHAEL ADDITION; ONE POT SYNTHESIS; PARTIAL DRUG SYNTHESIS; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REFORMATSKY REACTION;

EID: 56849117700 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-0028-1083539 Document Type: Article

Times cited : (7)

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- All compounds were characterized by IR, 1H NMR, 13C NMR, and MS analysis. Spectral Data Compound 8: 1H NMR (200 MHz, CDCl3, δ, 0.90 (t, J, 7.4 Hz, 3 H, 1.24 (t, J, 7.1 Hz, 3 H, 1.40 (t, J, 7.3 Hz, 3 H, 1.70-1.81 (m, 1 H, 1.92-2.04 (m, 1 H, 3.5 (t, J, 7.4 Hz, 1 H, 4.13 (q, J, 7.1, 2 H, 4.45 (q, J, 7.3 Hz, 2 H, 5.09 (d, J, 14.4 Hz, 1 H, 5.17 (d, J, 14.4 Hz, 1 H, 6.28 (d, J, 7.2 Hz, 1 H, 7.24 (d, J, 7.2 Hz, 1 H, 7.29-7.35 (s, 5H, Compound 9: 1H NMR (200 MHz, CDCl3, δ, 0.92 (t, J, 7.4 Hz, 3 H, 1.26 (t, J, 7.2 Hz, 3 H, 1.35 (t, J, 7.3 Hz, 3 H, 1.51-1.71 (m, 2 H, 1.82-1.96 (m, 1 H, 2.21-2.50 (m, 1 H, 3.22-3.42 (m, 2 H, 3.60-3.73 (m, 1 H, 4.15 (q, J, 7.2 Hz, 2 H, 4.36 (q, J, 7.3 Hz, 2 H, 4.49 (d, J, 14.7 Hz, 1 H, 4.66 d, J, 14.7 Hz
- 3OD): δ = 0.93 (t, J = 7.3 Hz, 3H), 1.86 (q, J = 7.2 Hz, 2 H), 5.22 (d, J = 16.2 Hz, 1 H), 5.41 (d, J = 16.2Hz, 1 H), 6.63 (d, J = 6.8 Hz, 1 H), 7.46 (d, J = 6.8 Hz, 1 H).

48
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- Typical Procedure for Compound 9 To a stirred solution of keto compound 10 (5 g, 29.4 mmol) in dry CH2Cl2 benzyl amine (3.21 mL, 29.4 mmol) was added dropwise at r.t. and allowed to stir for 20 min. After the completion of the reaction (TLC, K2CO3 (14.2 g, 102.9 mmol) was added followed by dropwise addition of ethyl malonyl chloride (4.89 mL, 38.22 mmol) at 0°C. The mixture was stirred at r.t. until completion (1 h, TLC, and then was filtered, and the residue was washed with CH2Cl2 (3 x 30 mL, The organic layer was washed with H2O, brine, dried over anhyd Na2SO4, filtered, and concentrated on a rotary evaporator under diminished pressure. The resulting residue was purified by flash column chromatography (silica gel) using EtOAc-PE (3:7) as an eluent, affording the dihydropyridone 9 as a colorless liquid 7.6 g, 70% yield
- 4, filtered, and concentrated on a rotary evaporator under diminished pressure. The resulting residue was purified by flash column chromatography (silica gel) using EtOAc-PE (3:7) as an eluent, affording the dihydropyridone 9 as a colorless liquid (7.6 g, 70% yield).

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