Daniel A. Dickman

Asymmetric synthesis of isoquinoline alkaloids

Abstract The use of chiral formamidines affixed to variously substituted tetrahydroisoquinolines, allows asymmetric C-C bond forming reactions to occur α- to the amino group. In this manner, a wide variety of (S)-1-alkyl-1,2,3,4-tetrahydroisoquinolines were constructed in > 90% enantiomeric excess. Choosing the proper substituents and skeletal features, an efficient entry into the benzylisoquinoline, tetrahydroprotoberberine, aporphine, and isopavine class of alkaloids was achieved.

Enzyme-catalyzed synthesis of optically Pure β-sulfonamidopropionic acids. Useful starting materials for P-3 site modified renin inhibitors.

Abstract The novel and efficient of several racemic β-sulfonamidopropionate esters is described. Treatment of the racemic esters with Chymotrypsin or Subtilisin Carlsberg (purified of detergent grade) provided the corresponding (S)-car☐ylic acids in 60–90% yield. These acids (75 to > 98% e.e.) are useful starting materials for the synthesis of P-3 site modified renin inhibitors.

An asymmetric synthesis of (+)-ocoteine

Abstract Using chiral formamidines, the synthesis of the title compound was accomplished in 93% ee. The asymmetric synthesis of l , via chiral formamidines was performed.