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DOI: 10.1055/s-0041-1738025
Total Synthesis of (±)-Reserpine
The Total Synthesis of Reserpine.
J. Am. Chem. Soc. 1956;
78: 2023-2025
DOI: 10.1021/ja01590a079.
The Total Synthesis of Reserpine.
Tetrahedron 1958;
2: 1-57
DOI: 10.1016/0040-4020(58)88022-9.
Key words
(±)-reserpine - indole alkaloids - Meerwein–Ponndorf–Verley reduction - Jones oxidation - Bischler–Napieralski reaction - Steglich esterificationSignificance
(±)-Reserpine was isolated from Rauvolfia serpentina, a flower from the Apocynaceae family. Today it is used as a drug for the treatment of high blood pressure. The configuration was elucidated in 1955 by the Ciba group. In 1956, Woodward and co-workers disclosed the first total synthesis, which completed (±)-reserpine in 21 steps.
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Comment
Lactone D is obtained through a Diels–Alder reaction of quinone A with diene B and subsequent reduction. Functional group interconversions lead to aldehyde I bearing five stereocenters. Reductive amination of I and indole derivative J, followed by lactamization forms K. Subsequent Bischler–Napieralski reaction completes the carbon skeleton of (±)-reserpine.
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Publication History
Article published online:
20 April 2022
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