SCOPUS 정보 검색 플랫폼

Volumn , Issue 7, 2008, Pages 1013-1016

Synthesis of C3-C12 fragment of 24-demethylbafilomycin C1 via anti-selective aldol condensation as the key stereocontrol step

(4) Dai, Wei Min a,b Feng, Gaofeng a,b Wu, Jinlong a Sun, Liang a,b

a ZHEJIANG UNIVERSITY (China)

b HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY (Hong Kong)

Author keywords

, unsaturated aldehyde; 1,3 diene; anti selective aldol; Dithiane; Horner Wittig olefination

Indexed keywords

24 DEMETHYLBAFILOMYCIN C 1; ALDEHYDE DERIVATIVE; ALKADIENE; ALKENE DERIVATIVE; KETONE DERIVATIVE; MACROLIDE; PHOSPHINE DERIVATIVE; PROPIONIC ACID;

ALDOL REACTION; ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRALITY; DRUG SYNTHESIS; HORNER REACTION; OLEFINATION; PROTON NUCLEAR MAGNETIC RESONANCE; RING CLOSING METATHESIS; STEREOCHEMISTRY;

EID: 42949105177 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1072504 Document Type: Article

Times cited : (9)

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- Procedure for Oxidation of the Alcohol 9 with Stabilized IBX to Form Aldehyde 10 To a solution of the alcohol 9 (1.990 g, 9.66 mmol) in DMSO (40 mL; without drying) was added stabilized IBX in six portions (45 wt, 1.002 x 6 g, 9.66 mmol, After each addition of stabilized IBX, the resultant mixture was stirred for 2 h at r.t. The reaction was quenched by aq Na 2S2O3 followed by addition of sat. aq NaHCO3. The aqueous mixture was extracted with EtOAc (100 x 2 mL) and the combined organic layer was dried over anhyd Na2SO4, filtrated, and concentrated under reduced pressure. The residue was purified by flash column chromatography (SiO2, 14% EtOAc in hexane) to provide the aldehyde 10 (1.399 g, 71% yield, Compound 10: yellow oil; [α]D20 -2.2 (c 1.35, CHCl3, 1H NMR (300 MHz, CDCl3, δ, 9.71 d, J, 1.8 H
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- We checked the diastereomeric ratio of the isolated aldol products prepared in several runs by 1H NMR spectroscopy and found that the ratio is about 95:5 in all cases. We did not obtain any separable minor diastereomers on the 3-gram-scale reaction, implying that the minor diastereomer is not separable from the major isomer
- 1H NMR spectroscopy and found that the ratio is about 95:5 in all cases. We did not obtain any separable minor diastereomers on the 3-gram-scale reaction, implying that the minor diastereomer is not separable from the major isomer.

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- 2, r.t.) and SIBX (DMSO, r.t.) oxidation was observed
- Epimerization of the aldehyde 20 obtained from both the DMP aq NaHCO3, We are not sure whether the epimerization occurred during the oxidation or over silica gel during column chromatographic separation
- 2, r.t.) and SIBX (DMSO, r.t.) oxidation was observed. The diastereomeric ratios are about 95:5. We are not sure whether the epimerization occurred during the oxidation or over silica gel during column chromatographic separation.
- The diastereomeric ratios are about , vol.95 , pp. 5

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- Physical and Spectroscopic Data of 3 Colorless oil; [α] D20 31.9 (c 0.73, CHCl3, 1H NMR (300 MHz, CDCl3, δ, 9.40 (s, 1 H, 6.72 (dd, J, 9.9, 1.2 Hz, 1 H, 6.61-6.48 (m, 1 H, 5.81 (d, J, 11.4 Hz, 1 H, 5.09 (dd, J, 16.8, 1.8 Hz, 1 H, 4.99 (d, J, 10.2 Hz, 1 H, 3.54 (dd, J, 4.5, 3.0 Hz, 1 H, 2.95-2.85 (m, 1 H, 2.19 (d, J, 8.4 Hz, 1 H, 1.85-1.64 (m, 2 H, 1.76 (s, 3 H, 1.71 (s, 3 H, 1.04 (d, J, 7.5 Hz, 3 H, 0.92 (s, 9 H, 0.74 (d, J, 6.3 Hz, 3 H, 0.07 (s, 3 H, 0.06 (s, 3 H, 13C NMR (75 MHz, CDCl3, δ, 195.6, 157.6, 137.3, 137.2, 133.0, 127.4, 115.0, 79.4, 43.7, 36.9, 35.9, 26.0 (x3, 18.6, 18.3, 16.3, 15.3, 9.3, 3.9, 4.0. HRMS ESI, m/z calcd for C21H39O2Si [M, H, 351.2719; found: 351.2729
- +]: 351.2719; found: 351.2729.

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