Date of Award:

5-1988

Document Type:

Thesis

Degree Name:

Master of Science (MS)

Department:

Chemistry and Biochemistry

Committee Chair(s)

Daniel L. Comins (Committee Chair)

Committee

Daniel L. Comins

Committee

Joseph G. Morse

Committee

Richard K. Olsen

Abstract

The most efficient and stereoselective total synthesis of (+/-) lausbine II to date has been achieved. The key steps in this are the copper-mediated conjugate addition reaction of the Grignard reagent of 1-bromo-4-chlorobutane to a dihydropyridone and a stereoselective reduction of a quinolizidinone.

Methodology has been developed for the convenient synthesis of 1-acyl-2-substituted-1,2,5,6-tetrahydropyridines. This was accomplished by adding novel alkylzinc iodides to the 1-acyliminium ion derived from Nphenoxycarbonyl-4-methoxy-1, 2, 3, 4-tetrahydropyridine.

Checksum

959f500c38598b6e4bcef3c63dab2b78

Included in

Chemistry Commons

Share

COinS