220106-55-8

Upstream product

• 22002-45-5 2-bromo-4-methylanisole 
• 3740-59-8 3,4-dihydro-6-methyl-2H-pyran-2-one 
• 6627-55-0 2-bromo-p-cresol 
• 3128-06-1 5-ketohexanoic acid 

Downstream Products

• 220106-58-1 1-methoxy-4-methyl-2-(1,2,2-trimethylcyclopentyl)-benzene 
• 81784-10-3 1S-(2'-hydroxy-5'-methylphenyl)-1,2,2-trimethylcyclopentane 

Relevant academic research and scientific papers

A short synthesis of α-herbertenol featuring the use of a dihydropyranone as a 1,5-diketone synthon

The paper describes a short synthesis of α-herbertenol. Key features are the addition of dihyropyranone 5 to an aryllithium to give 1,5-diketone 7; a titanium(O) mediated cyclisation of 7 to diol 8 and a sequential methylation of 8 to herbertenol methyl ether 9.

1,5-diketones from 3,4-dihydropyranones: An application in the synthesis of (±)-α-herbertenol

An approach to 1,5-diketones involving the addition of organolithium reagents to 3,4-dihydropyranones is described. Good yields are obtained when reactions are quenched with trimethylsilyl chloride prior to hydrolytic work up and the organolithium reagent contains a Lewis basic group adjacent to the carbon to lithium bond. The method has been applied in a short synthesis of the fungicidal sesquiterpene (±)-α-herbertenol.