502-33-0

Upstream product

• 18913-31-0 2,3-butadien-1-ol 
• 114846-91-2 4-methyl-3-penten-2-one dimethyl ketal 
• 58193-39-8 8-chloro-2,6-dimethyl-octa-2,6-dien-4-one 
• 66680-86-2 isobutenyltributyltin 
• 3350-78-5 3,3-Dimethylacryloyl chloride 
• 539-70-8 2-Methyl-6-methylene-2,7-octadien-4-one 
• 78-79-5 isoprene 
• 60857-00-3 Acetic acid (Z)-3,7-dimethyl-5-oxo-octa-3,6-dienyl ester 

Downstream Products

• 65442-32-2 (Z)-2,6-dimethyl-5,7-octadien-4-ol 
• 112369-53-6 2,6-dimethylocta-5(E),7-dien-4-ol 
• 58558-48-8 (E)-2,6-dimethyl-octa-1,5,7-trien-4-ol 
• 14314-21-7 (+/-)-ipsenol 
• 206115-88-0 (3E,5E)-2,6-dimethyl-3,5,7-octatriene-2-ol 
• 16750-87-1 (+/-)-filifolon 
• 529-01-1 isopiperitenone 
• 71539-59-8 Bis(trans-ocimenon) 

Relevant academic research and scientific papers

Total synthesis and biological evaluation of methylgerambullone

First total synthesis of methylgerambullone (MGB, 1) isolated from Glycosmis angustifolia was completed via a convergent route. The effect of MGB on the contractile responses of the isolated guinea-pig ileum induced by acetylcholine was investigated. As a result, it showed a potent relaxation rate (78.66 ± 4.30% at 100 mg/L) in a concentration-dependent manner on longitudinal smooth muscle contraction of isolated guinea-pig ileum induced by 1 μM acetylcholine.

Stereospecific synthesis of (Z) or (E)-3-methylalk-2-enoic acids

The palladium catalysed coupling of organozinc or organotin reagents with 3-iodobut-2(or 3)-enoic acid is stereoselective and affords Z (or E)-3-methylalk-2-enoic acids. The method was applied to the synthesis of the E and Z stereoisomers of ocimenones and pseudo-tagetones.

Reactions with α,β-Unsaturated Nitrile Oxides. Synthetic Studies in the Terpene Field. Synthesis of Tagetones, Ocimenones, Deodarone and Atlantone

The generation and 1,3-dipolar cycloaddition of α,β-unsaturated nitrile oxides are described.Selective reductive cleavage of the isoxazoline ring was achived.Subsequent elimination of water leads to the 1,4-dien-3-one system.The formation of tetrahydro-γ-pyrones is observed.The reactions were applied to the synthesis of tagetones, ocimenones, deodarone and atlantone.

Claisen Rearrangements with Mesityl Oxide Dimethyl Ketal. Synthesis of Ipsdienone, E- and E-Ocimenone, 2,6-Dimethyl-2,7-octadien-4-one and 2,6-Dimethyl-2,7-octadien-4-ol

4-Methyl-3-penten-2-one (mesityl oxide) dimethyl ketal was synthesized and utilizied in Claisen rearrangements with 2,3-butadien-1-ol and 2-buten-1-ol to form ipsdienone and 2,6-dimethyl-2,7-octadien-4-one, from which the ocimenones and 2,6-dimethyl-2,7-octadien-4-ol were prepared.

Terpenes and Terpene Derivatives, XVII. - Thermal and AlCl3-Catalyzed Reaction of Ocimenone

Bis(trans-ocimenone) (5),reported to be a naturally occuring compound, is formed by thermal dimerization of (E)-ocimenone (E-4). - Treatment of 4 with AlCl3 leads, in addition to unchanged 4, to a mixture of the rearranged products filifolone (6) and rac-