Synthesis of Enantiomerically Pure Building Block for Tolyporphins

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Synthesis of an Enantiomerically Pure Ring A building block for Tolyporphin and Tolyporphin Derivatives

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.

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