19464-85-8

Basic information

• Product Name: roccellaric acid
• Synonyms: roccellaric acid;(2R)-2α-Tridecyl-4α-methyl-5-oxooxolane-3β-carboxylic acid;(2R)-Tetrahydro-4α-methyl-5-oxo-2α-tridecyl-3β-furancarboxylic acid;2α-Tridecyl-4α-methyl-5-oxooxolane-3β-carboxylic acid;Rocellaric acid
• CAS NO: 19464-85-8
• Molecular Formula: C19H34O4
• Molecular Weight: 326.47086
• Mol File: 19464-85-8.mol
• Article Data: 13

Chemical Properties

• Appearance: /
• CAS DataBase Reference: roccellaric acid(CAS DataBase Reference)
• NIST Chemistry Reference: roccellaric acid(19464-85-8)
• EPA Substance Registry System: roccellaric acid(19464-85-8)

Safety Data

• Hazardous Substances Data: 19464-85-8(Hazardous Substances Data)

Upstream product

• 493-46-9 (+)-protolichesterinic acid 
• 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 
• 2765-11-9 n-pentadecanal 
• 180267-10-1 (3S,4S,5R)-4-((1S)-1,2-dihydroxyethyl)-3-methyl-5-tridecyldihydrofuran-2-one 
• 165605-86-7 (3S,4S,5R)-3-Methyl-4--5-tridecyl-4,5-dihydro-2(3H)-furanone 

Relevant articles and documents

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.

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.

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.