کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5223347 1383484 2009 17 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Enantioselective synthesis of 11-substituted 2- or 3-methoxy-17-vinylgona-1,3,5(10)-trien-13-ols
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Enantioselective synthesis of 11-substituted 2- or 3-methoxy-17-vinylgona-1,3,5(10)-trien-13-ols
چکیده انگلیسی

The acylation of the (±)-spiro-γ-lactone 1 lithium enolate (3 equiv) by the O-TBDMS methyl (−)-(S)-lactate, the O-TBDMS methyl (+)-(S)-mandelate, or the diacetone-d-glucose carbonate (1 equiv each) occurs with a kinetic resolution. The (S,S)-enolate is the most reactive with the lactate and it is the (R,R)-enolate, which selectively reacts with the mandelate or the DAG carbonate. After alkylation of the resulting acyl lactones with 4- or 5-methoxy-1-iodobenzocyclobutene and heating, title compounds were obtained and, after deprotection, the structures of the optically pure new steroids were ascertained by single crystal X-ray analysis.

Figure optionsDownload as PowerPoint slide

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 65, Issue 1, 3 January 2009, Pages 177–193