459-92-7

Upstream product

• 29021-40-7 3,7-Dimethyl-7-octen-1-in-3-ol 
• 75697-97-1 (Z)-3,7-dimethyl-2,7-octadienal 
• 74514-16-2 (E)-6-chloro-3,7-dimethylocta-2,7-dienal 
• 106-24-1 Geraniol 
• 74514-18-4 (E)-6-chloro-3,7-dimethylocta-2,7-dien-1-ol 
• 97344-88-2 isopentenylmagnesium bromide 
• 1222538-34-2 diethyl acetal of 3-(bromomethyl)but-3-enal 
• 20038-12-4 4-bromo-2-methylbut-1-ene 
• 110995-23-8 ethyl 7-methyl-3-oxo-7-octenate 
• 110995-22-7 Ethyl 3,7-dimethyl-2ξ,7-octadienoate 
• 14459-10-0 (E)-3,7-dimethyl-2,7-octadien-1-ol 
• 1376709-31-7 (Z)-ethyl 7-methyl-3-(((trifluoromethyl)sulfonyl)oxy)octa-2,7-dienoate 
• 141-27-5 3,7-dimethyl-2,6-octadienal 

Downstream Products

• 75697-97-1 (Z)-3,7-dimethyl-2,7-octadienal 
• 75698-04-3 3-(1',2'-Dimethyl-2'-cyclopenten-1'-yl)propanal 
• 1376709-22-6 C₃₃H₄₄O₅ 

Relevant academic research and scientific papers

Total synthesis of alotaketal A

The total synthesis of the cAMP signaling pathway activator (-)-alotaketal A is reported. A convergent approach to the unusual alotane sesterterpenoid skeleton was employed, exploiting a remarkable LiDBB-mediated coupling of an (R)-carvone-derived δ-lactone with an allyl bromide side chain, followed by spiroacetalization.

7-METHYL-3-METHYLENE-7-OCTENAL ACETAL COMPOUND AND METHODS FOR PRODUCING ALDEHYDE COMPOUND AND ESTER COMPOUND USING THE SAME

There are provided methods of efficiently producing compounds that are, for example, sex pheromones of San Jose Scale. For example, there is provided a method for producing a 7-methyl-3-methylene-7-octenyl carboxylate compound (4), the method including the steps of: hydrolyzing a 7-methyl-3-methylene-7-octenal acetal compound (1) to obtain 7-methyl-3-methylene-7-octenal (2); reducing the 7-methyl-3-methylene-7-octenal (2) to obtain 7-methyl-3-methylene-7-octenol (3); and esterifying the 7-methyl-3-methylene-7-octenol (3) to obtain a 7-methyl-3-methylene-7-octenyl carboxylate compound (4).

Total synthesis and structure-activity relationship study of the potent cAMP signaling agonist (-)-alotaketal A

A detailed account of the first total synthesis of alotaketal A, a tricyclic spiroketal sesterterpenoid that potently activates the cAMP signaling pathway, is provided. The synthesis employs both intra- and intermolecular reductive allylation of esters for assembling one of the fragments and their coupling. A Hg(OAc)2-mediated allylic mercuration is used to introduce the C22-hydroxyl group. The subtle influence of substituents over the course of the spiroketalization process is revealed. The synthesis confirms the relative and absolute stereochemistry of (-)-alotaketal A and allows verification of alotaketal A's effect over cAMP signaling using reporter-based FRET imaging assays with HEK 293T cells. Our studies also revealed alotaketal A's unique activity in selectively targeting nuclear PKA signaling in living cells. The Royal Society of Chemistry 2013.

Total synthesis of alotaketal A

The total synthesis of the cAMP signaling pathway activator (-)-alotaketal A is reported. A convergent approach to the unusual alotane sesterterpenoid skeleton was employed, exploiting a remarkable LiDBB-mediated coupling of an (R)-carvone-derived δ-lactone with an allyl bromide side chain, followed by spiroacetalization.

Total synthesis of the potent cAMP signaling agonist (-)-Alotaketal A

We have developed a convergent synthetic route to the potent cAMP signaling agonist (-)-alotaketal A that employs two stages of SmI2-mediated reductive allylation reactions for assembling the polycycle and fragment coupling. Also notable are a Hg(OAc)2-mediated selective alkene oxidation and the subtlety of the formation of the unprecedented spiroketal ring system. The probes AKAR4 and ICUE3 were used to evaluate the cAMP singaling agonistic activity of (-)-alotaketal A and elucidate its structure-activity relationship.

THE REACTION OF HYPOCHLOROUS ACID WITH OLEFINS. A CONVENIENT SYNTHESYS OF ALLYLIC CHLORIDES

The reaction of HOCl with more highly substituted olefins in methylene chloride affords allylic chlorides in 60-80percent isolated yields.The utility of the reaction is illustrated with the synthesis of Rose oxide and α-monoterpenes.

PHOTOCHEMISCHE REAKTIONEN

On 1n,?*-excitation (λ>347 nm) citral (5) and the methyl ketone 10 isomerize to compounds A (7, 19) and B(6, 20), whereas the phenyl ketone 11 changes into the isomer 24 of type E. evidence is given that the conversion to A and B may arise from the 3n,?*-state of the 2,6-diene-carbonyl compounds.On 1p,?*-excitation (λ=254 nm) 5 and 10 yield the isomers A (7, 19) and D (18, 22), but no products of type B.Futhermore, conversion of 10 to the isomer 21 of type C is observed.Selective 1?,?*-excitation (λ=254 nm) as well as selective 1n,?*-excitation (λ>347 nm) of the 2,7-diene-carbonyl compounds 12 and 13 give rise to isomerization to the compounds F (25, 28), exclusively.The intramolecular (2+2)-photocycloadditions are shown to be triplet processes.UV.-irradiation (λ>280 nm) of compounds F (25, 28) furnishes the isomeric products G (26, 29) which photoisomerize to oxetanes of type H (27, 30).