Total Synthesis of the Norhasubanan Alkaloid Stephadiamine

Hartrampf, Nina; Winter, Nils; Pupo, Gabriele; Stoltz, Brian M.; Trauner, Dirk (2018): Total Synthesis of the Norhasubanan Alkaloid Stephadiamine. In: Journal of the American Chemical Society, Vol. 140, No. 28: pp. 8675-8680

Abstract

(+)-Stephadiamine is an unusual alkaloid isolated from the vine Stephania japonica. It features a norhasubanan skeleton, and contains two adjacent alpha-tertiary amines, which renders it an attractive synthetic target. Here, we present the first total synthesis of stephadiamine, which hinges on an efficient cascade reaction to implement the aza[4.3.3]propellane core of the alkaloid. The alpha-aminolactone moiety in a highly hindered position was installed via Tollens reaction and Curtius rearrangement. Useful building blocks for the asymmetric synthesis of morphine and (nor)hasubanan alkaloids are introduced.

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• ISSN: 0002-7863
• Language: English