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Synlett
Volumn , Issue 10, 2007, Pages 1537-1540
Synthetic studies on a marine natural product, palmerolide A: Synthesis of C1-C9 and C15-C21 fragments
Author keywords

Cross metathesis; Grubbs' catalyst; Marine natural product; Mitsunobu reaction; Pd(II) catalyzed allylic rearrangement
Indexed keywords

NATURAL PRODUCT; PALLADIUM; PALMEROLIDE A; POLYKETIDE; UNCLASSIFIED DRUG;
EID: 34347355537     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-982539     Document Type: Article
Times cited : (37)
References (23)
  • 10
    • 34347346774 scopus 로고    scopus 로고
    • Experimental Procedure for Compound 18 To a solution of acetate 17 (230 mg, 0.54 mmol) in anhyd THF (10 mL) was added PdCl 2(MeCN)2 (6 mg, 4 mol, at 0°C under nitrogen. After being stirred at 0°C for 30 min, the mixture was further stirred at r.t. for another 1 h. The solvent was evaporated and the residue was further purified by flash chromatography (silica gel, 5-10% EtOAc-hexanes) to afford the E/Z mixture of acetate (200 mg, 0.47 mmol, 87, To a solution of the above acetate (160 mg, 0.37 mmol) in CH2Cl2 (3.4 mL) and buffer (pH 7, 390 μL) was added DDQ (102 mg, 0.45 mmol) at 0°C. After being stirred at the same temperature for 1 h, the reaction mixture was quenched with sat. NaHCO3 (8 mL) and the aqueous layer was extracted with CH 2Cl2 4 x 10 mL, The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo. The resi
    • 3).
  • 22
    • 34347361236 scopus 로고    scopus 로고
    • Procedure for the Synthesis of Compound 28 A solution of methyltriphenylphosphonium bromide (273 mg, 0.76 mmol) in dry toluene (12 mL) was heated to reflux and about 10 mL of toluene were distilled off azeotropically to remove moisture. To the above suspension was added KOt-Bu (86 mg, 0.76 mmol, the mixture was stirred at 105°C for 1 h, and then cooled to 0°C. A solution of aldehyde (180 mg, 0.58 mmol) in dry toluene (0.5 mL) was added dropwise to the above suspension with stirring, and the resulting mixture was stirred at 0°C for 1 h. After addition of sat. NH4Cl (5 mL, the resulting mixture was extracted with EtOAc (3 x 10 mL, The combined organic layers were washed with brine, dried over Na 2SO4 and concentrated in vacuo. The resulting residue was purified by flash column chromatography (silica gel, 5-15% EtOAc-hexanes) to give 28 (116 mg, 0.38 mmol, 65% for two steps) as a colorless oil. Rf, 0.5
    • 3).
  • 23
    • 34347346773 scopus 로고    scopus 로고
    • Spectral Data for Selected Compounds Data for ketone 11: Rf, 0.34 (30% EtOAc-hexanes, 1H NMR (400 MHz, CDCl3, δ, 8.24 (dt, J, 8.8, 2.1 Hz, 2 H, 8.12 (dt, J, 9.2, 2.2 Hz, 2 H, 7.29-7.23 (m, 5 H, 5.72 (dt, J, 7.7, 5.1 Hz, 1 H, 4.46 (s, 2 H, 3.42 (d, J, 6.2 Hz, 2 H, 2.93 (dd, J, 16.5, 7.7 Hz, 1 H, 2.82 (dd, J, 16.5, 5.5 Hz, 1 H, 2.26-2.19 (m, 1 H, 2.17 (s, 3 H, 1.06 (d, J, 7.0 Hz, 3 H, 13C NMR (100 MHz, CDCl3, δ, 205.1, 163.9, 150.4, 138.0, 135.6, 130.6, 128.2, 127.6. 127.5, 123.4, 73.1, 72.7, 71.9, 45.7, 37.1, 30.1, 12.1. IR (neat, 2933, 2863, 1725, 1607, 1528, 1411, 1349, 1275, 1169, 1102 cm-1. HRMS (ESI-TOF, m/z calcd for [C21H23O6N, Na, 408.1423; found: 408.1422, α]D 20-10.7 c 0.67, CHCl3, Data for compound 12
    • 3).

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.