A Concise Synthesis of (±)-Cacalol

A simple synthesis of the natural product cacalol has been developed that proceeds in seven steps and 21−25% overall yield. Ortho-lithiation of 4-methylanisole and alkylation with 5-iodo-1-pentene, followed by intramolecular Friedel−Crafts alkylation, gave 5-methoxy-1,8-dimethyltetralin. This compou...

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Bibliographic Details
Published in:Journal of organic chemistry 2008-07, Vol.73 (13), p.5177-5179
Main Authors: Kedrowski, Brant L, Hoppe, Robert W
Format: Article
Language:English
Subjects:
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Exact sciences and technology
Molecular Structure
Organic chemistry
Preparations and properties
Sesquiterpenes - chemical synthesis
Terpenoids
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Summary:A simple synthesis of the natural product cacalol has been developed that proceeds in seven steps and 21−25% overall yield. Ortho-lithiation of 4-methylanisole and alkylation with 5-iodo-1-pentene, followed by intramolecular Friedel−Crafts alkylation, gave 5-methoxy-1,8-dimethyltetralin. This compound was then formylated in the 6-position. Baeyer−Villiger oxidation and hydrolysis of the resulting formate gave 6-hydroxy-5-methoxy-1,8-dimethyltetralin. Alkylation of the phenolic hydroxyl group with chloroacetone followed by cyclodehydration gave cacalol methyl ether. Deprotection of this aryl methyl ether yielded cacalol.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo800324c