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• 1277166-98-9 C₂₀H₃₆O₄ 
• 1277166-91-2 (4S,5S,E)-4,5-(isopropylidenedioxy)pentadec-2-en-1-ol 
• 1277166-90-1 (4R,5S)-5-[(S)-1-hydroxyundecyl]-4-vinyl-4,5-dihydrofuran-2(3H)-one 
• 1277166-95-6 S-methyl O-(S)-1-[(2S,3R)-5-oxo-3-vinyltetrahydrofuran-2-yl]undecyl carbonodithioate 
• 1277167-03-9 (4R,5R)-5-tridecyl-4-vinyl-4,5-dihydrofuran-2(3H)-one 
• 1277166-92-3 ethyl 4-hydroxypentadec-2-ynoate 
• 1277166-93-4 (4S,5S,E)-ethyl 4,5-dihydroxypentadec-2-enoate 
• 112-54-9 Dodecanal 
• 244612-58-6 (2R,3S)-5-oxo-2-tridecyl-tetrahydrofuran-3-carboxylic acid 
• 74-88-4 methyl iodide 
• 493-46-9 tetrahydro-4-methylene-5-oxo-2-tridecyl-3-furancarboxylic acid 
• 220344-53-6 tert-butyl-(4-chloro-1-tridecyl-but-2-ynyloxy)-dimethyl-silane 

Relevant academic research and scientific papers

Stereoselective total synthesis of (+)-nephrosteranic acid and (+)-roccellaric acid through asymmetric dihydroxylation and Johnson-Claisen rearrangement

An efficient stereoselective total synthesis of (+)-nephrosteranic acid and (+)-roccellaric acid is presented. The synthetic strategy features the regioselective asymmetric dihydroxylation of the γ,δ-olefinic bond of a α,β,γ,δ-unsaturated ester and the Johnson-Claisen rearrangement as the key steps. The synthesis is achieved in 10 steps and 6.8% (nephrosteranic acid) and 7.6% (roccellaric acid) overall yield.

Stereodivergent Synthesis of Chiral Paraconic Acids via Dynamic Kinetic Resolution of 3-Acylsuccinimides

A direct N-heterocyclic carbene (NHC) catalysis of maleimides with alkyl aldehydes is established for the synthesis of 3-acylsuccinimides. The first dynamic kinetic resolution of 3-acylsuccinimides is accomplished through asymmetric transfer hydrogenation. These two catalytic methodologies are utilized for the synthesis of each enantiomer of trans-paraconic acids in three steps and cis-paraconic acids in four steps with good yields and high stereoselectivities. This stereodivergent synthetic methodology is applied for the synthesis of seven bioactive paraconic acid natural products.

A protecting-group-free synthesis of (+)-nephrosteranic, (+)-protolichesterinic, (+)-nephrosterinic, (+)-phaseolinic, (+)-rocellaric acids and (+)-methylenolactocin

A collective synthesis of a γ-butyrolactone class of paraconic acids such as (+)-methylenolactocin, (+)-phaseolinic acid, (+)-nephrosteranic acid, (+)-nephrosterinic acid, (+)-rocellaric acid and (+)-protolichesterinic acid is described. The strategy adopted is protecting-group-free based on efficient Pd-catalyzed Suzuki-Miyaura coupling and Ru-catalyzed Sharpless oxidation to construct the core β-CO2H-γ-butyrolactone unit to accomplish the synthesis of various paraconic acids.

General enantioselective synthesis of butyrolactone natural products via ruthenium-SYNPHOS-catalyzed hydrogenation reactions

Enantioselective syntheses of several paraconic acids have been achieved using catalyzed asymmetric hydrogenation of β-keto esters with SYNPHOS as a ligand. This strategy allowed the short synthesis of biologically active (-)-methylenolactocin 1, (-)-protolichesterinic acid 2, (-)-phaseolinic acid 3 and (+)-roccellaric acid 4.

Enantioselective butenolide preparation for straightforward asymmetric syntheses of γ-lactones - Paraconic acids, avenaciolide, and hydroxylated eleutherol

The naturally occurring γ-lactones (+)-methylenolactocin (13) and its enantiomer, (+)-protolichesterinic acid (14) and its enantiomer, (+)-rocellaric acid (15), and the methylene bis(γ-lactone) (-)-avenaciolide (16) were synthesized with 95-98 % ees in very few steps. Enantiocontrol was imposed by the asymmetric dihydroxylation of trans-configured β,γ-unsaturated carboxylic esters (namely compounds 1i, 1j, and 1n) with AD mix-α [for the levorotatory target structures, except for (-)-avenaciolide] or AD mix-β [for the dextrorotatory target structures plus (-)-avenaciolide]. β,γ-Unsaturated carboxylic ester 1e required increased amounts of the oxidant and auxiliary to produce the hydroxy lactone R,R-3e, a precursor of the naphtho-γ-lactone (+)-9-hydroxyeleutherol (12; 96 % ee). Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Vicinal dianion of triethyl ethanetricarboxylate: Syntheses of (±)-lichesterinic acid, (±)-phaseolinic acid, (±)-nephromopsinic acid, (±)-rocellaric acid, and (±)-dihydroprotolichesterinic acid

The vicinal dianion 2 derived from triethyl ethanetricarboxylate reacted regioselectively with aldehydes and ketones at C(β) to provide paraconic acid derivatives 5a-f in moderate to high yields as mixtures of diastereoisomers. The paraconic acid derivatives 5e and 5f were utilized as the starting materials for the syntheses of (±)-lichesterinic acid (12), (±)-phaseolinic acid (13), (±)-nephromopsinic acid (14), (±)-rocellaric acid (15), and (±)-dihydroprotolichesterinic acid (16).

Asymmetric carbolithiation of 2-phenylselenofumarate derivatives: A short synthesis of (-)-roccellaric acid

(-)-Roccellaric acid and variously substituted succinates are obtained through direct asymmetric carbolithiation of 2-phenylselenofumarate derivatives, followed by reaction with suitable electrophiles.

Total synthesis of (±)-dihydroprotolichesterinic acid and formal synthesis of (±)-Roccellaric acid by radical cyclisation of an epoxide. Using a transition-metal radical source

A short and efficient total synthesis of (±)-Dihydroprotolichesterinic acid (1) and Formal synthesis of (±)-Roccellaric acid (2) has been achieved by radical cyclisation of epoxide using a transition metal radical source.

Efficient total syntheses of (±)protolichesterinic acid and (±)rocellaric acid via tungsten-π-allyl complexes

Total syntheses of racemic protolichesterinic acid (1) and rocellaric acid (2) were achieved with the use of tungsten-π-allyl complex in the key step. In this synthetic route, compounds 1 and 2 were prepared in four and six steps respectively starting from readily available chloropropargyl derivatives.