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Synfacts 2024; 20(01): 0007
DOI: 10.1055/s-0043-1772888
Synthesis of Natural Products

Total Synthesis of (±)-Marasmic Acid

Contributor(s):
Erick M. Carreira
,
Sander Folkerts
Greenlee WJ, Woodward RB. Harvard University, Massachusetts, USA
Marasmic acid–II: Total synthesis of (±)-marasmic acid.

Tetrahedron 1980;
36: 3367-3375
DOI: 10.1016/0040-4020(80)80187-6.
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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.


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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.


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Publication History

Article published online:
08 December 2023

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