کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5216616 1383270 2013 6 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Practical synthesis of C1-8 fragment of autolytimycin via a chelation-controlled diastereoselective addition of diisopropenylzinc to α-methoxy aldehyde
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Practical synthesis of C1-8 fragment of autolytimycin via a chelation-controlled diastereoselective addition of diisopropenylzinc to α-methoxy aldehyde
چکیده انگلیسی

The C1-8 fragment of autolytimycin was synthesized via a reliable 10-step route capable of delivering 41% overall yield at multi-gram scale. As a key step, a chelation-controlled isopropenylation of α-oxygenated aldehydes was established with a reagent combination of diisopropenylzinc, magnesium halide, and a dichloromethane/toluene mixed solvent. Cram-chelate isopropenylation products dominated for aldehydes with a small α-substituents, such as -OMe and -OBn groups, while the Felkin product could be obtained with a bulky -OTBS group.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 69, Issue 45, 11 November 2013, Pages 9463-9468
نویسندگان
, , , , , ,