125276-88-2

Upstream product

• 70908-42-8 α,α-dimethyl allyl methyl carbonate 
• 63721-05-1 methyl 3,3-dimethyl-4-penteneoate 
• 119548-51-5 methyl 3,3-dimethylhepta-1-ene-6-yne-4-carboxylate 
• 74866-35-6 2-(1,1-dimethylallyl)malonic acid dimethyl ester 
• 227596-86-3 2,2-dimethyl-5-dimethoxymethyl-3-(tert-butyldimethylsilyloxymethyl)cyclopentanone 
• 239085-69-9 3,3-dimethyl-1,4-dihydroxymethylcyclopentene 
• 239085-68-8 3,3-dimethyl-4-hydroxymethylcyclopent-1-ene-carboxaldehyde 
• 129881-58-9 2,2-dimethyl-3-<(t-butyldimethylsiloxy)methyl>cyclopentanone 
• 129881-65-8 2,2-dimethyl-3-hydroxymethyl cyclopentanone 

Downstream Products

• 104104-38-3 (3,4,5,5-tetramethylcyclopent-2-enyl)methanol 
• 135305-29-2 (-)-γ-necrodol 
• 135413-42-2 (-)-α-epi-necrodol 

Relevant academic research and scientific papers

A Synthesis of β-Necrodol Via A Palladium Catalyzed Reductive Enyne Cyclization

The Pd catalyzed reductive enyne cyclization provides an approach to control 1,3-diastereoselectivity and thereby provides a five step synthesis of β-necrodol, a key substituent of the defensive secretion of the red-lined carrion beetle.

Synthesis and bioassay of racemic and chiral trans -α-Necrodyl Isobutyrate, the sex pheromone of the grape mealybug pseudococcus maritimus

A concise synthesis of the racemic form of the female-produced pheromone of the grape mealybug was developed. The synthesis was readily adapted to production of both enantiomers of the pheromone via lipase-catalyzed kinetic resolution of an intermediate in the synthesis. Replicated field trials revealed that, contrary to a preliminary report, the (R,R)- rather than the (S,S)-enantiomer is the attractive stereoisomer. Lithium aluminum hydride reduction of the insect-produced compound to α-necrodol followed by analysis on a chiral stationary phase GC column showed that the insect-produced material was actually an 85:15 mixture of the (R,R)- and (S,S)-enantiomers. The racemic form of the pheromone was highly attractive to male mealybugs, and in one of two field bioassays, the racemic material was significantly more attractive than the pure (R,R)-enantiomer, suggesting that the (S,S)-enantiomer might act synergistically.

High diastereoselectivity in Claisen rearrangement in a sterically congested cyclopentane system. Total synthesis of (±)-β-necrodol

Total synthesis of the monoterpene β-necrodol has been accomplished. The key step involves an ortho-ester Claisen rearrangement in a highly sterically congested cyclopentane derivative resulting in a high level of 1,3-trans diastereoselection. A novel photo-induced decarboxylation of the obtained γ,δ-unsaturated acid afforded β-necrodol.

Stereocontrolled total synthesis of (±)-β-necrodol

A total synthesis of racemic β-necrodol is described using an ortho- ester Claisen rearrangement as the key step to dictate a high level of trans- 1,3-diastereoselection on a cyclopentane derivative.