کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5230753 1383705 2007 9 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Formal syntheses of (−)- and (+)-aphanorphine from (2S,4R)-4-hydroxyproline
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Formal syntheses of (−)- and (+)-aphanorphine from (2S,4R)-4-hydroxyproline
چکیده انگلیسی

We describe the efficient formal syntheses of both natural (−)-aphanorphine and unnatural (+)-aphanorphine from the same commercially available amino acid, (2S,4R)-4-hydroxyproline. The tricyclic framework was constructed by intramolecular Friedel-Crafts reaction. (1R,4S)-1-Methyl-8-methoxy-3-(4-toluenesulfonyl)-2,3,4,5-tetrahydro-1,4-methano-3-benzazepine (8) was synthesized in six steps from sulfonamide 3; (−)-aphanorphine methyl ether 24 was obtained in seven steps from lactone 10. Intramolecular etherification of 18 proceeded with excellent stereoselectivity in the presence of BF3·OEt2, which has paved an efficient synthetic route to a series of medicinally attractive heterocycles.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 63, Issue 32, 6 August 2007, Pages 7523-7531
نویسندگان
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