Total Synthesis of (+)-Asteriscanolide

Key words

(+)-asteriscanolide - sesquiterpene - electrocyclization - cycloaddition - Cope rearrangement - cyclobutadiene

Significance

Snapper and Limanto present a concise synthesis of the sesquiterpene (+)-asteriscanolide. The authors use a combination of different pericyclic reactions to assemble the eight-membered ring of the natural product in an elegant fashion. Their work showcases the use of iron-complexed cyclobutadienes in total synthesis.

Comment

A photochemical electrocyclization of α-pyrone A followed by CO₂ elimination furnished iron-complexed cyclobutadiene B. Further functionalization gave access to cycloaddition precursor G. Cyclobutadiene cycloaddition, followed by ring-opening metathesis and Cope rearrangement quickly assembled cyclooctadiene J which was converted into (+)-asteriscanolide in four steps.

Publication History

Article published online:
18 August 2022