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Synthesis of Enantiomerically Pure Building Block for Tolyporphins



Год выпуска: 2010
Автор: Genevieve Etornam Adukpo and Franz-Peter Montforts
Издательство: LAP Lambert Academic Publishing
Страниц: 112
ISBN: 9783843362191
Описание
The enantiomerically pure pyrrolidine diester (Ring A) is a useful building block for the synthesis of chiral tolyporphin and other hydroporphyrin compounds. This was synthesized from enantiomerically pure lactam-lactone. Treatment of optically active aromatic amines with bislactone gave pairs of N-alkylated lactam-lactone diastereomers. These diastereomers were separated by MPL chromatography and debenzylated using ceric (IV) ammonium nitrate (CAN) to yield enantiomerically pure lactam-lactone isomers. The (–)-lactam-lactone enantiomer was treated with methanolic cyanide solution which selectively opened lactone ring to form the cyano lactam. This was further transformed into the cis- and trans-thiocyanolactam isomers. The configurations of these isomers were established by NOE experiment which was confirmed by X-ray measurement and theoretical means(ab initio calculations). Coupling of cis-thiocyanolactam with bromomalonic diester according to the sulphide ...


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Юлия, добрый вечер, спасибо большое! Ваши консультации по философии психоанализа отличные, с их помощью написала 3 эссе, все были оценены на 5! :))