کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5230965 1383711 2007 8 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
An enantioselective total synthesis of pinnaic acid
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
An enantioselective total synthesis of pinnaic acid
چکیده انگلیسی

An enantioselective and convergent total synthesis of marine natural product pinnaic acid has been achieved. Our general synthetic approach is featured with an asymmetric hydrogenation of racemic γ-keto ester 3, a diastereoselective methylation on the α-methylene of the (1R,5R)-lactone 4, and a diastereoselective Michael addition of the tertiary nitro cyclopentane. The central azaspiro[4.5]decane was constructed utilizing reductive cyclization of the δ-nitroketone followed by highly stereoselective reduction of the cyclic imine with NaBH4. Ultimately, successive use of triethyl-2-phosphonopropionate and Heathcock's phosphorane 18 to elaborate C5 and C13 side chains completed the total synthesis of pinnaic acid.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 63, Issue 28, 9 July 2007, Pages 6454-6461
نویسندگان
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