کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5220245 | 1383382 | 2011 | 14 صفحه PDF | دانلود رایگان |
عنوان انگلیسی مقاله ISI
Synthesis of the C(1)-C(16) fragment of bryostatins using an 'ene' reaction between an allylsilane and an alkynone
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کلمات کلیدی
موضوعات مرتبط
مهندسی و علوم پایه
شیمی
شیمی آلی
پیش نمایش صفحه اول مقاله
![عکس صفحه اول مقاله: Synthesis of the C(1)-C(16) fragment of bryostatins using an 'ene' reaction between an allylsilane and an alkynone Synthesis of the C(1)-C(16) fragment of bryostatins using an 'ene' reaction between an allylsilane and an alkynone](/preview/png/5220245.png)
چکیده انگلیسی
The zinc(II) iodide mediated 'ene' reaction between (4R)-4,5-bis-(tert-butyldimethylsilyloxy)-2-(trimethylsilylmethyl)pent-1-ene (43) and (5S,7R,9S)-5,11-dibenzyloxy-4,4-dimethyl-7,9-dihydroxy-7,9-O-isopropylideneundec-1-yn-3-one (53) gave the (E)-vinylsilane 54 with excellent stereoselectivity. Simultaneous deprotection and cyclisation via a stereoselective oxy-Michael reaction gave the bicyclic acetal 57 after treatment with trimethyl orthoformate. A synthesis of the ester 60 corresponding to the C(1)-C(16) fragment of the bryostatins was then completed by O-silylation, oxidative cleavage of the methylene group and a stereoselective condensation of the resulting ketone 59 with the chiral phosphonate 61.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 67, Issue 52, 30 December 2011, Pages 10068-10081
Journal: Tetrahedron - Volume 67, Issue 52, 30 December 2011, Pages 10068-10081
نویسندگان
Matthew O'Brien, Eric J. Thomas,