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 |
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Faculties: | Chemistry and Pharmacy > Department of Chemistry |
Subjects: | 500 Science > 540 Chemistry |
ISSN: | 0002-7863 |
Language: | English |
Item ID: | 67500 |
Date Deposited: | 19. Jul 2019, 12:22 |
Last Modified: | 04. Nov 2020, 13:49 |