76280-88-1

Upstream product

• 4342-60-3 4-methylcyclohex-3-enecarboxylic acid 
• 6090-08-0 (R)-2-methyl-2-(4-methylcyclohex-3-en-1-yl)-1,3-dioxolane 
• 6090-11-5 3-(4-methyl-cyclohex-3-enyl)-3-oxo-propionic acid ethyl ester 
• 78-79-5 isoprene 
• 24903-94-4 7-methyl-1,6-octadiene-3-one 
• 6090-09-1 (+-)-4-acetyl-1-methylcyclohexene 
• 870-63-3 prenyl bromide 
• 64504-53-6 2-methylpent-2-en-5-yl lithium 
• 16695-95-7 (4'-methylcyclohex-3'-ene-1-'-yl)carbonyl chloride 
• 82096-08-0 5-Methyl-1-(4-trimethylsilanylmethyl-cyclohex-3-enyl)-hex-4-en-1-one 
• 115-18-4 2-methyl-3-buten-2-ol 
• 79673-97-5 1-(1-Oxo-2-methylsulfinylethyl)-4-methyl-3-cyclohexen 

Downstream Products

• 4891-79-6 β-bisabolene 
• 515-69-5 bisabolol 

Relevant academic research and scientific papers

Regioselective α-alkylation of silyl enolates using a mild catalyst- ZnCl2 doped on acidic alumina

ZnCl2 doped acidic alumina used as a solid support acts as a better Lewis acid in the S(N)1 reaction of trimethyl silyl enol ethers with 30, allylic and benzylic halides to yield exclusively the substituted product in excellent yields. This method has been employed for the synthesis of monocyclic sesquitepene hydrocarbon, (+)-β-bisabolene and a monoterpene, 2,6-dimethyl-7-octen-4-one.

Termite trail attractants: New synthesis of racemic (E)-α-, (Z)-α- and β-bisabolenes

Racemic (E)-α-bisabolene (E)(1) was synthetized starting from 4-methyl-3-cyclohexenecarboxylic acid (3) by a reaction sequence involving the Pd(0)-catalyzed cross-coupling reaction between the (E)-2-methyl-1-alkenyltrimethylstannane 8 and 3-methyl-2-buten-1-yl acetate (9). Three different procedures, in which a common precursor was used as key intermediate, were tested for the synthesis of racemic (Z)-α-bisabolene (Z)(1). The best one, which involved the reaction between bromide 18 and lithium dialkenylcuprate 19, afforded a mixture of (Z)- and (E)-1 in a 93:7 molar ratio, respectively. Finally, racemic β-bisabolene (2) was synthetized by a simple reaction sequence involving the Zr-promoted methylenation of ketone 22 prepared from 3.

ORGANOMANGANESE (II) REAGENTS XIV: A SHORT AND EFFICIENT SYNTHESIS OF DIASTEREOISOMERIC (+/-)-α-BISABOLOLS AND (+/-)-CHLORPHENOXAMINE

Diastereomeric (+/-)-α-bisabolols (7), a sesquiterpenoid alcohol, and (+/-)-chlorphenoxamine (12), an antihistamine, have been prepared in excellent yields.Both these short and convenient syntheses involve as a key step the one-pot elaboration of a dissymetrical tertiary alcohol via an organomanganese reagent (5 to 7 and 9 to 10 respectively).

CHEMISTRY OF THE ORGANOSILICON COMPOUNDS-165 2-TRIMETHYLSILYL-METHYL-1, 3-BUTADIENE-A VERSATILE BUILDING BLOCK FOR TERPENE SYNTHESIS

Two types of synthetically useful reactions of 2-trimethylsilylmethyl-1,3-butadiene (7) are discussed.Reactions of 7 with acid chlorides, aldehydes, ketones and acetals activated by a Lewis acid give isoprenylated compounds, while 7 undergoes the Diels-Alder reaction whit dienophiles.High regiospecificity of the reaction qualifies 7 for a versatile building block of terpene synthesis.

HIGHLY REGIOSELECTIVE DIELS-ALDER REACTIONS OF 2-TRIMETHYLSILYLMETHYL-1,3-BUTADIENE CATALYZED BY A LEWIS ACID AND APPLICATIONS TO SYNTHESES OF TERPENES

2-Trimethylsilylmethyl-1,3-butadiene undergoes highly regioselective Diels-Alder reactions with dienophiles such as acrolein and methyl vinyl ketone catalyzed by aluminium chloride in which the "para" isomers are obtained almost exclusively.The adducts are converted readily to a variety of naturally occurring mono and sesquiterpenes.