Total Synthesis of (±)-Progesterone

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.

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.

Publikationsverlauf

Artikel online veröffentlicht:
16. Februar 2022