TOTAL SYNTHESIS OF (±)-4-DEOXYBLENNOLIDE C VIA SPIROCHROMANONE

We report the total synthesis of (+/-)-4-deoxyblennolide C, a deoxy analogue of xanthone antibiotics blennolide C isolated from the fermentation broth of Blennoria sp. The synthesis involves construction of a quaternary carbon during the formation of spirochromanone through the aldol reaction of o-hydroxyacetophenones and cyclohexenone, oxidative cleavage of the alkene moiety, and the construction of a xanthone framework by Dieckmann condensation.

Automated summary

The total synthesis of (+/-)-4-deoxyblennolide C was achieved by constructing a quaternary carbon, oxidative cleavage of alkene moiety, and the formation of xanthone framework. This work provides a method to prepare deoxy analogues of xanthone antibiotics.