SYNTHESIS OF (+/-)-TRANS-6-[4,4-BIS(4-FLUOROPHENYL)-3-(1-METHYL-1H-TETRAZOL-5-YL)-1(E),3-[2-C-14]BUTADIENYL]-4-HYDROXY-3,4,5,6-TETRAHYDRO-2H-PYRAN-2-ONE

被引：1
|
作者：
LUKE, GM
SWIGOR, JE
机构：
[1] Bristol-Myers Squibb, Pharmaceutical Research and Development Division, Syracuse, New York
来源：
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS | 1991年 / 29卷 / 02期
关键词：
(+/-)-TRANS-6-[4,4-BIS(4-FLUOROPHENYL)-3-(1-METHYL-1H-TETRAZOL-5-YL)-1(E),3-[2-; HMG-COA REDUCTASE INHIBITOR; HYPOCHOLESTEROLEMIC;
D O I：
10.1002/jlcr.2580290209
中图分类号：
Q5 [生物化学];
学科分类号：
071010 ; 081704 ;
摘要：
A convergent synthesis of the title compound (BMY-22089) is described. [C-14]Methyl iodide was used to alkylate 1,5-dimethyltetrazole which was added to 4,4'-difluorobenzophenone to give the tertiary alcohol 4. Dehydration gave the olefin 5 which was brominated and converted to the phosphonate 7 with trimethylphosphite. Coupling of the carbanion of 7 with cis-2, 2-dimethyl-6-formyl-1,3-dioxane-4-acetic acid tert-butyl ester (8) produced the diene 9. Sequential hydrolysis steps using acid and base gave the dihydroxy acid 11 which was converted to the lactone 12 with the use of dicyclohexylcarbodiimide. The overall yield was 20%.
引用
收藏
页码：193 / 199
页数：7
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