Synthesis of Enantiomerically Pure Building Block for Tolyporphins (Paperback)

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 contraction method gave the enantiomerically pure pyrrolidine diester.

General

Imprint:	Lap Lambert Academic Publishing
Country of origin:	Germany
Release date:	October 2010
First published:	October 2010
Authors:	Genevieve Etornam Adukpo • Franz-Peter Montforts
Dimensions:	229 x 152 x 7mm (L x W x T)
Format:	Paperback - Trade
Pages:	112
ISBN-13:	978-3-8433-6219-1
Categories:	Books > Science & Mathematics > Chemistry > Organic chemistry > General
LSN:	3-8433-6219-X
Barcode:	9783843362191

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