58775-54-5

Upstream product

• 504-02-9 1,3-cylohexanedione 
• 5323-87-5 3-Ethoxycyclohex-2-en-1-one 
• 106-95-6 allyl bromide 

Downstream Products

• 4166-61-4 4-allyl-2-cyclohexenone 
• 58775-63-6 rac-4-allyl-3-methylcyclohex-2-enone 
• 1108084-76-9 6-allyl-6-(3,4-dimethoxyphenyl)-3-ethoxy-cyclohex-2-enone 
• 13481-16-8 4-methyl-4-(prop-2-enyl)cyclohex-2-en-1-one 
• 871468-73-4 4-allyl-4-[4-(4-methoxy-benzyloxy)-butyl]-cyclohex-2-enone 
• 871468-72-3 6-allyl-3-ethoxy-6-[4-(4-methoxy-benzyloxy)-butyl]-cyclohex-2-enone 
• 125408-50-6 (6-Allyl-3-ethoxy-3-methyl-cyclohex-1-enyloxy)-trimethyl-silane 

Relevant academic research and scientific papers

A total synthesis of sarcandralactone A: A general, concise, RCM enabled approach to lindenanolide sesquiterpenoids

A total synthesis of lindenane-type sesquiterpenoid natural product sarcandralactone A and its close sibling 5-epi-shizukanolide has been accomplished through a concise strategy in which a one-pot γ-lactone annulation and a RCM reaction constitute pivotal

Protecting-Group-Free Total Synthesis of (–)-Pallambins A—D

A full account of the total synthesis of (–)-pallambins A—D (1—6) is described. The strategy was devised by simulating their biosynthetic pathway. The left-part bicyclo[3.2.1]octane system of pallambins C and D was efficiently constructed via a palladium- catalyzed oxidative cyclization. For construction of the right-part tetrahydrofuran/γ-lactone moiety (C/D rings), initial attempts to synthesize the allylic alcohol 15 for an one-step Pd-mediated alkoxycarbonylation have failed. However, during the course of this work, an unprecedented CH3Li-mediated method for conversion of bromoisoxazoline to the corresponding β-hydroxy nitrile has been discovered. Furthermore, a stepwise protocol was designed, namely an Eschenmoser-Claisen rearrangement/Lactonization to generate the C ring, and a non-classical Wittig reaction to form the D ring. During the course of this work, a palladium-catalyzed method for dehydrobromination of bromide ketone was developed. Finally, an individual transformation of pallambins C (3) and D (4) generated pallambins A (5) and B (6) under mild UV irradiation. Thus, the first enantioselective total syntheses of (–)-pallambins A—D have been achieved in 15 or 16 steps from the known chiral cyclohexenone 8. The described synthesis avoids protecting-group manipulations by designing highly chemo- and stereoselective transformations.

Palladium-Catalyzed α-Arylation of Vinylogous Esters for the Synthesis of γ,γ-Disubstituted Cyclohexenones

A palladium-catalyzed α-arylation of cyclic vinylogous esters to form products that are converted in one step to γ-alkyl-γ-aryl-substituted cyclohexenones is reported. This Pd-catalyzed reaction proceeds at room temperature, is generally high-yielding, and uses an amount of a commercially available catalyst as low as 0.25 mol %. The scope of aryl bromides is particularly broad, and alkenyl bromides can also be used. This two-step protocol, comprising α-arylation and reductive transposition, can be performed in one pot and is applicable to gram-scale synthesis.

Synthesis and pharmacology of 1-deoxy analogs of CP-47,497 and CP-55,940

A series of 1-deoxy analogs of CP-47,497 (8 and 13, n = 0-7) and 1-deoxy analogs of CP-55,940 (9, n = 0-7) have been synthesized and their affinities for the cannabinoid CB1 and CB2 receptors have been determined. Although the majori

Mn(III)-based C-C bond formation: Regioselective α′-allylation of various α,β-unsaturated, α and β-alkoxy α,β-unsaturated ketones

The Manganese(III)-based regioselective α′-keto radical generation of unsaturated ketones is a versatile synthetic procedure with broad applicability. The generated α′-keto radical slowly creates a metal enolate in a solvent at reflux. The resultant metal

Ring Opening of Cyclopropylketones Induced by Photochemical Electron Transfer

Depending on the substitution pattern of cyclopropylketones, the photochemically induced electron transfer of tertiary amines to cyclopropylketones leads either to the formation of 3-substituted cycloalkanones or to ring expanded products.

Pyrazolopyridine cycloalkanones and process for their preparation

Novel tetrahydropyrazolo-[3,4-b]quinolinones, cyclopenta[b]pyrazolo-[4,3-e]pyridinones and cyclohepta[b]-pyrazolo[4,3-e]pyridinones, useful as anxiolytics having reduced side effects, are disclosed, including methods of preparation, pharmaceutical compositions containing them and intermediates used in their preparation.