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Synfacts 2022; 18(07): 0719
DOI: 10.1055/s-0041-1738545
Synthesis of Natural Products and Potential Drugs

Synthesis of (±)-Quadrone

Contributor(s):
Erick M. Carreira
,
Bilal Kicin
Takeda K, Shimono Y, Yoshii E. * Toyama Medical and Pharmaceutical University, Japan
A Short-Step Entry to (±)-Quadrone.

J. Am. Chem. Soc. 1983;
105: 563-568
DOI: 10.1021/ja00341a042.
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Key words

(±)-quadrone - sesquiterpene - [2+2] cycloaddition - Wagner–Meerwein rearrangement - Kucherov reaction - aldol condensation - Jones oxidation

Significance

The sesquiterpene (±)-quadrone was isolated from Aspergillus terreus in 1978 and exhibits antitumor properties. Structurally, the natural product contains a quadracyclic fused ring system around a central quarternary carbon atom. In 1983, Yoshii and co-workers presented a formal synthesis, featuring a Wagner–Meerwein rearrangement.


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Comment

Cyclobutane C was accessed through photochemical [2+2] cycloaddition and transformed into alcohol G in three steps. Wagner–Meerwein rearrangement and subsequent oxi­dation yielded alkyne H. Kucherov reaction to ­diketone I enabled aldol condensation to enone J. Deprotection followed by Jones oxidation gave ­access to carboxylic acid K, which was previously transformed to the natural product by Danishefsky and co-workers in three steps.


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Publication History

Article published online:
15 June 2022

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