Total Synthesis of (±)-Marasmic Acid

Key words

(±)-marasmic acid - fungal metabolite of Basidiomycetes - Diels–Alder reaction - alkylative cyclopropanation

Significance

The authors present the synthesis of (±)-marasmic acid, one of the fungal metabolites isolated from Basidiomycetes. The structure features a hydrindane with a cis relationship between the cyclopropane ring and the vicinal hydrogen at the ring fusion.

Comment

The synthetic endeavors start with a Diels–Alder reaction that results in two inconsequential regioisomers. Convergent alkylative cyclopropanation of the mixture gives a single tetracylic product H. Diol J is converted to the corresponding dichloroformate L and subsequently oxidized to obtain dialdehyde M. Finally, treatment with trifluoroacetic acid affords (±)-marasmic acid.

Publication History

Article published online:
08 December 2023