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Synfacts 2021; 17(03): 0251
DOI: 10.1055/s-0040-1720304
DOI: 10.1055/s-0040-1720304
Synthesis of Natural Products and Potential Drugs
Total Synthesis of (±)-Strychnine
Rawal VH,
*,
Iwasa S.
Ohio State University, Columbus, USA
A Short, Stereocontrolled Synthesis of Strychnine.
J. Org. Chem. 1994;
59: 2685-2686
DOI: 10.1021/jo00089a008.
A Short, Stereocontrolled Synthesis of Strychnine.
J. Org. Chem. 1994;
59: 2685-2686
DOI: 10.1021/jo00089a008.
Key words
(±)-strychnine - cyclopropyl–iminium rearrangement - Diels–Alder cycloaddition - Jeffrey–Heck reaction
Significance
The heptacyclic alkaloid strychnine has been the focus of numerous synthetic efforts over the last 75 years since the first total synthesis by Woodward. In 1994, Rawal and Iwasa reported a concise, stereo-controlled total synthesis of racemic strychnine notable for its elegance.
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Comment
Elaboration of starting material A to aniline C involves a cyclopropyl-iminium rearrangement. After alkylation to yield E, Diels–Alder cycloaddition gives rise to carbamate F. The Jeffrey modification of the Heck reaction yields advanced intermediate I, which is then converted to the natural product.
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Publication History
Article published online:
16 February 2021
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