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Enantiocontrolled synthesis of burseran, brassilignan, dehydroxycubebin, and other tetrahydrofuran lignans in both enantiomeric forms. Application of intermolecular nitrile oxide cycloadditions and lipase-mediated kinetic resolutions

التفاصيل البيبلوغرافية
العنوان: Enantiocontrolled synthesis of burseran, brassilignan, dehydroxycubebin, and other tetrahydrofuran lignans in both enantiomeric forms. Application of intermolecular nitrile oxide cycloadditions and lipase-mediated kinetic resolutions
المؤلفون: Janet A. Gaboury, Mukund P. Sibi
المصدر: The Journal of Organic Chemistry. 58:2173-2180
بيانات النشر: American Chemical Society (ACS), 1993.
سنة النشر: 1993
مصطلحات موضوعية: biology, Nitrile, Organic Chemistry, Triacylglycerol lipase, Cycloaddition, Kinetic resolution, chemistry.chemical_compound, chemistry, biology.protein, Organic chemistry, Lipase, Enantiomer, Enantiomeric excess, Tetrahydrofuran
الوصف: Several natural and unnatural tetrahydrofuran lignans have been synthesized by a convergent approach. Our methodology utilizes a nitrile oxide cycloaddition to dihydrofuran 8 and an enzymatic resolution of 3-hydroxytetrahydrofurans 11 by lipase PS. The lipase-mediated kinetic resolution of alcohols 11 furnished both enantiomers of the lignan precursors 12 and 14 in high optical purity (>99% ee). This is followed by a S N 2 displacement of tosylates 15 and 18 by α-lithiobenzyl phenyl sulfides. In this manner, both enantiomers of 3,4-dibenzyltetrahydrofuran (17a, 20a), 3,4-bis(3-methorybenzyl)tetrahydrofuran (17b, 20b), brassilignan (17c, 20c), dehydrorycubebin (17d, 20d), and burseran (17e, 20e) were synthesized in overall yields of 6-16%
تدمد: 1520-6904
0022-3263
URL الوصول: https://explore.openaire.eu/search/publication?articleId=doi_________::607425021abaf2ea44c6a6a8ec92920a
https://doi.org/10.1021/jo00060a037
رقم الأكسشن: edsair.doi...........607425021abaf2ea44c6a6a8ec92920a
قاعدة البيانات: OpenAIRE
الوصف
تدمد:15206904
00223263