552855-46-6

Upstream product

• 1193-55-1 2-methylcyclohexane-1,3-dione 
• 107-02-8 acrolein 

Downstream Products

• 1315210-92-4 C₁₁H₁₅BrO₂ 
• 1315211-03-0 C₁₁H₁₅BrO₂ 
• 1315210-90-2 C₁₁H₁₄Br₂O₂ 
• 1393100-31-6 C₂₃H₃₀O₃S 
• 1393100-29-2 C₁₉H₂₂O₃S 
• 1393100-27-0 C₁₉H₂₂O₃S 
• 1393100-33-8 C₁₄H₂₀O₃S 
• 1393100-45-2 C₂₅H₃₄O₃S 
• 909726-56-3 methyl (E)-5-(1-methyl-2,6-dioxocyclohexyl)pent-2-enoate 
• 1416969-74-8 (4aS,5S,6R,8aS)-5-[(4-chlorophenyl)carbonyl]-4a,6-dihydroxy-8a-methyldecahydronaphthalen-1-one 
• 1416969-91-9 (4aS,5S,6R,8aS)-5-(4-chlorobenzoyl)-4a-hydroxy-8a-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)octahydronaphthalen-1(2H)-one 
• 1416969-83-9 2-[(E)-5-(3-trifluoromethylphenyl)-5-oxopent-3-enyl]-2-methylcyclohexane-1,3-dione 
• 1416970-00-7 (4aR,5S,6R,8aR)-5-(2-bromobenzoyl)-4a-hydroxy-8a-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)octahydronaphthalen-1(2H)-one 
• 1416970-02-9 (4aS,5S,6R,8aS)-5-(2-bromobenzoyl)-4a-hydroxy-8a-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)octahydronaphthalen-1(2H)-one 

Relevant academic research and scientific papers

Domino Michael-aldol annulations for the stereocontrolled synthesis of bicyclo[3.3.1]nonane and bicyclo[3.2.1]octane derivatives

Domino Michael-aldol annulation of cycloalkane-1,3-diones with enals affords a general route to 6-hydroxybicyclo[3.3.1]nonane-2,9-diones and 2-hydroxybicyclo[3.2.1]octane-6,8-diones, notably in one-pot procedures under convenient conditions. The annulation is shown to be compatible with one or more substituents at six positions of the bicyclo[3.3.1]nonane-2,9-dione scaffold. In some cases, the relative configuration of the product can be controlled by the appropriate choice of solvent, base and temperature for the annulation. In contrast to the chair-chair conformations usually adopted, the bicyclo compounds derived from 2,4,4-trimethylcyclohexane-1,3-dione possessed boat-chair conformations. Oxidation of the annulation products gave the corresponding bicyclo triketones.

Convenient preparation of synthetically useful chiral quaternary carbon-containing bicyclic compounds with organocatalysts

Chiral quaternary carbon-containing bicyclic compounds possessing carbonyl functionalities were efficiently synthesized through asymmetric intramolecular aldol reactions with organocatalysts. Bicyclo [3.3.0] and [3.4.0] systems were constructed with a dia

Enantio- And Diastereoselective Construction of Contiguous Tetrasubstituted Chiral Carbons in Organocatalytic Oxadecalin Synthesis

The organocatalytic enantio- and diastereoselective cycloetherification of 1,3-cyclohexanedione-bearing enones involving the in situ generation of chiral cyanohydrins was developed. This transformation offers the first catalytic asymmetric approach to oxa

Synthesis of (-)-mitrephorone A via a bioinspired late stage C-H oxidation of (-)-mitrephorone B

We present a bioinspired late-stage C-H oxidation of the ent-trachylobane natural product mitrephorone B to mitrephorone A. The realization of this unprecedented transformation was accomplished by either an iron-catalyzed or electrochemical oxidation and enabled access to the densely substituted oxetane in one step. Formation of mitrephorone C, which is lacking the central oxetane unit but features a keto-function at C2, was not formed under these conditions.

Concise Enantioselective Synthesis of Oxygenated Steroids via Sequential Copper(II)-Catalyzed Michael Addition/Intramolecular Aldol Cyclization Reactions

A new scalable enantioselective approach to functionalized oxygenated steroids is described. This strategy is based on chiral bis(oxazoline) copper(II) complex-catalyzed enantioselective and diastereoselective Michael reactions of cyclic ketoesters and enones to install vicinal quaternary and tertiary stereocenters. In addition, the utility of copper(II) salts as highly active catalysts for the Michael reactions of traditionally unreactive β,β′-enones and substituted β,β′-ketoesters that results in unprecedented Michael adducts containing vicinal all-carbon quaternary centers is also demonstrated. The Michael adducts subsequently undergo base-promoted diastereoselective aldol cascade reactions resulting in the natural or unnatural steroid skeletons. The experimental and computational studies suggest that the torsional strain effects arising from the presence of the Δ5-unsaturation are key controlling elements for the formation of the natural cardenolide scaffold. The described method enables expedient generation of polycyclic molecules including modified steroidal scaffolds as well as challenging-to-synthesize Hajos-Parrish and Wieland-Miescher ketones.

An easy route toward enantio-enriched polycyclic derivatives via an asymmetric domino conjugate reduction-aldol cyclization catalyzed by a chiral Cu(I) complex

A highly efficient reductive-aldol cyclization mediated by a chiral Cu(I) complex and an organosilane yielded to cyclic or polycyclic derivatives. An excellent control of the selectivities was reached in most cases (dr up to 100:0 and ee up to 95%). After

Desymmetrizing reductive aldol cyclizations of enethioate derivatives of 1,3-diones catalyzed by a chiral copper hydride

A range of enethioate derivatives of 1,3-diones underwent reductive aldol cyclizations catalyzed by a chiral copper hydride generated in situ from 5 mol% TaniaPhos (SL-T001-1), 5 mol% Cu(OAc)2·H2O, 5 mol% bipyridine and 2.0 equiv. of PhSiH3, to furnish polycyclic β-hydroxythioester products bearing three newly established contiguous stereocenters, with >98:2 dr and in up to 94% yield and 98% ee. The use of an amine such as bipyridine or 2,6-lutidine as additive results in an increase of the overall reaction rate. The major bicyclic aldol product has all substituents cis and can be rationalized by a reductively generated (Z)-enolate reacting with the dione via a cyclic transition state.

Toward an integrated route to the vernonia allenes and related sesquiterpenoids

The synthesis of a model endocyclic allene related to the vernonia allenes is described. Fragmentation of a suitable decalin derivative gave the simplified germacrane scaffold. Computational analysis of this and related substrates provides insight into th

Synthesis of racemic and enantiomerically pure acetylenic -keto esters derived from 2-methyl-1,3-cycloalkanediones and 2-methylcycloalkanones respectively

Racemic and enantiomerically pure alkynyl esters tethered, respectively, to 2-methyl-1,3-cycloalkanediones and 2-methylcycloalkanones were readily obtained starting from common intermediates, which were available on large scale.

Efficient construction of polycyclic derivatives via a highly selective cui-catalyzed domino reductive-aldol cyclization

A versatile methodology for the diastereo-and enantioselective domino reductive-aldol cyclizations is reported. By using a copper (l)/diphosphane ligand, various five-and six-membered rings were generated with good to excellent diastereo-and enantioselect