Total Synthesis of (±)-Antheridium-Inducing Factor A_An

Key words

(±)-antheridium-inducing factor A_An - plant hormone - vinylcyclopropane rearrangement - Prilezhaev epoxidation - Diels–Alder reaction

Significance

Corey and Myers reported the total synthesis and structural revision of (±)-antheridium-inducing factor A_An. The natural product is a plant hormone which stimulates development of sex organs in some ferns. Their synthetic strategy centers around an intramolecular cyclopropanation reaction mediated by copper complex E, a Lewis acid promoted vinylcyclopropane rearrangement and a Diels–Alder reaction with nitroethene (I) to access the core of the natural product.

Comment

The synthesis commenced with allylation of aryl iodide A and nickel complex B. Intramolecular cyclopropanation of diazo D mediated by copper complex E followed by bromination and elimination furnished diene F. Treatment with diethyl aluminum chloride initiated vinylcyclopropane rearrangement to skipped diene G. Diene H, accessed through epoxidation and elimination of G, underwent Diels–Alder reaction with nitroethene (I) to nitroalkane K, which was subsequently converted into ketone L.

Publikationsverlauf

Artikel online veröffentlicht:
15. November 2023