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Synfacts 2022; 18(05): 0473
DOI: 10.1055/s-0041-1738025
Synthesis of Natural Products and Potential Drugs

Total Synthesis of (±)-Reserpine

Contributor(s):
Erick M. Carreira
,
Willi M. Amberg
Woodward RB, *, Bader FE, Bickel H, Frey AJ, Kierstead RW. Harvard University, Cambridge, USA
The Total Synthesis of Reserpine.

J. Am. Chem. Soc. 1956;
78: 2023-2025
DOI: 10.1021/ja01590a079.
CrossrefGoogle Scholar
Woodward RB, *, Bader FE, Bickel H, Frey AJ, Kierstead RW. Harvard University, Cambridge, USA
The Total Synthesis of Reserpine.

Tetrahedron 1958;
2: 1-57
DOI: 10.1016/0040-4020(58)88022-9.
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Key words

(±)-reserpine - indole alkaloids - Meerwein–Ponndorf–Verley reduction - Jones oxidation - Bischler–Napieralski reaction - Steglich esterification

Significance

(±)-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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