Total Synthesis of (±)-Ambiguine P

Keywords

(±)-ambiguine P - hapalindole-type alkaloids - Fischer indole synthesis - Cope rearrangement - Prins-type cyclization - Friedel–Crafts alkylation

Significance

Yang and Li report the total synthesis of hapalindole-type alkaloid (±)-ambiguine P. Characterized by their 6–5–6–7–6-pentacyclic scaffold, ambiguines are the most structurally complex members of this family. (–)-Ambiguine P has been isolated from the cyanobacterium Fischerella ambigua and members of the ambiguine family have exhibited antimicrobial activity.

 

MissingLinkText

Comment

The indole of (±)-ambiguine P was assembled via Fischer indole synthesis, followed by C3-geranylation. Construction of the carbon scaffold of the natural product was completed via a Cope/Prins/Friedel–Crafts cascade reaction, yielding the pentacyclic intermediate G. Subsequent desaturation and oxidation reactions completed the synthesis of (±)-ambiguine P in six steps from ketone A.

 

MissingLinkText

 

MissingLinkText

Publication History

Article published online:
23 July 2025