Total Synthesis of (+)-Dihydropleurotinic Acid

Key words

(+)-dihydropleurotinic acid - pleurotin natural products - Johnson–Claisen rearrangement - photocatalytic radical cyclization - Pinnick oxidation - benzylic oxidation/ etherification

Significance

Ding, Xuan, and co-workers present the total synthesis of four pleurotin natural products. The natural products featuring a 5/6/6/6-tetracyclic carbon skeleton were assembled through Johnson–Claisen rearrangement, photocatalytic radical cyclization and benzylic oxidation/etherification.

Comment

The allylic alcohol D was converted into the ester F by Johnson–Claisen rearrangement. Subsequent hydroboration and elaboration gave rise to aldehyde H, which underwent radical cyclization under blue light irradiation in the presence of Ir-photoctalyst I, thiol J and pyrrolidine to afford aldehyde K.

Publication History

Article published online:
16 August 2024