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DOI: 10.1055/s-0041-1737869
Total Synthesis of (±)-Progesterone
Acetylenic Bond Participation in Biogenetic-Like Olefinic Cylizations. II. Synthesis of dl-Progesterone.
J. Am. Chem. Soc. 1971;
93: 4332-4334
DOI: 10.1021/ja00746a062.
Key words
(±)-progesterone - steroids - Johnson–Claisen rearrangement - Wittig reaction - polyene cyclization - aldol condensation
Significance
In 1971, Johnson and co-workers published the total synthesis of racemic progesterone relying on a biomimetic, cationic polyene–cyclization. Similar polyene cyclizations have been used frequently in the total synthesis of various natural products ever since Johnson's seminal studies.
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Comment
The synthesis relies on a convergent coupling of aldehyde C and Wittig reagent F to yield diketal G. Elaboration into cyclization precursor J enables the key acid-mediated polyene cyclization forging three rings and setting six stereocenters with excellent diastereocontrol. Ozonolysis of olefin L followed by aldol condensation yields racemic progesterone.
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Publication History
Article published online:
16 February 2022
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