کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5225034 1383536 2007 13 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Total synthesis of Amaryllidaceae alkaloids, (+)-vittatine and (+)-haemanthamine, starting from d-glucose
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Total synthesis of Amaryllidaceae alkaloids, (+)-vittatine and (+)-haemanthamine, starting from d-glucose
چکیده انگلیسی

The stereoselective total synthesis of (+)-vittatine 1 and (+)-haemanthamine 2 starting from d-glucose is described. The cyclohexene ring in 1 was prepared in an optically active form from d-glucose using Ferrier's carbocyclization reaction, and the critical quaternary carbon was stereoselectively generated via chirality transfer by the Claisen rearrangement of cyclohexenol 6. The hexahydroindole skeleton was effectively constructed by the intramolecular aminomercuration-demercuration of 14, followed by Chugaev reaction to provide 16. Finally, Pictet-Spengler reaction completed the first chiral synthesis of (+)-vittatine 1. On the other hand, the α-hydroxylation of the ester 5 stereoselectively proceeded to give α-hydroxy ester 19, to which was introduced an amino function to provide 4. A similar transformation of 4, as employed in the synthesis of vittatine, furnished (+)-haemanthamine 2.

The stereoselective total synthesis of (+)-vittatine 1 and (+)-haemanthamine 2 starting from d-glucose is described. The quaternary carbons in 1 and 2 were stereoselectively generated via chirality transfer by way of Claisen rearrangement of cyclohexenol, prepared in an optically active form from d-glucose using Ferrier's carbocyclization reaction. The hexahydroindole skeleton was constructed by intramolecular aminomercuration-demercuration, followed by Chugaev reaction.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 63, Issue 30, 23 July 2007, Pages 6977-6989
نویسندگان
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