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Total Synthesis of the Norhasubanan Alkaloid Stephadiamine.

ABSTRACT: (+)-Stephadiamine is an unusual alkaloid isolated from the vine Stephania japonica. It features a norhasubanan skeleton, and contains two adjacent ?-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 ?-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.

SUBMITTER: Hartrampf N

PROVIDER: S-EPMC6130314 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature

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Total Synthesis of the Norhasubanan Alkaloid Stephadiamine.

Hartrampf Nina N Winter Nils N Pupo Gabriele G Stoltz Brian M BM Trauner Dirk D

Journal of the American Chemical Society 20180709 28

(+)-Stephadiamine is an unusual alkaloid isolated from the vine Stephania japonica. It features a norhasubanan skeleton, and contains two adjacent α-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 α-aminolactone moiety in a highly hindered position was installed via Tollens reaction and Curtius rearrangement. ...[more]

PMID: 29889502

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