Roccellaric acid
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| Category | Others |
| Catalog number | BBF-05031 |
| CAS | 19464-85-8 |
| Molecular Weight | 326.47 |
| Molecular Formula | C19H34O4 |
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Specification
| Synonyms | 3-Furancarboxylic acid, tetrahydro-4-methyl-5-oxo-2-tridecyl-, [2R-(2α,3β,4α)]-; (2R,3S,4S)-Tetrahydro-4-methyl-5-oxo-2-tridecyl-3-furancarboxylic acid; (+)-Roccellaric acid; Dihydroneoprotolichesteric acid; Nephromopsinic acid (-) |
| IUPAC Name | (2R,3S,4S)-4-methyl-5-oxo-2-tridecyloxolane-3-carboxylic acid |
| Canonical SMILES | CCCCCCCCCCCCCC1C(C(C(=O)O1)C)C(=O)O |
| InChI | InChI=1S/C19H34O4/c1-3-4-5-6-7-8-9-10-11-12-13-14-16-17(18(20)21)15(2)19(22)23-16/h15-17H,3-14H2,1-2H3,(H,20,21)/t15-,16+,17-/m0/s1 |
| InChI Key | WLGALFYTFVOQPY-BBWFWOEESA-N |
Properties
| Melting Point | 110-111°C |
Reference Reading
1. Free-radical-mediated conjugate additions. Enantioselective synthesis of butyrolactone natural products: (-)-enterolactone, (-)-arctigenin, (-)-isoarctigenin, (-)-nephrosteranic acid, and (-)-roccellaric acid
Mukund P Sibi, Pingrong Liu, Jianguo Ji, Saumen Hajra, Jian-xie Chen J Org Chem. 2002 Mar 22;67(6):1738-45. doi: 10.1021/jo015501x.
Lewis acid-mediated conjugate addition of alkyl radicals to a differentially protected fumarate 10 produced the monoalkylated succinates with high chemical efficiency and excellent stereoselectivity. A subsequent alkylation or an aldol reaction furnished the disubstituted succinates with syn configuration. The chiral auxiliary, 4-diphenylmethyl-2-oxazolidinone, controlled the stereoselectivity in both steps. Manipulation of the disubstituted succinates obtained by alkylation furnished the natural products (-)-enterolactone, (-)-arctigenin, and (-)-isoarctigenin. The overall yields for the target natural products were 20-26% over six steps. Selective functionalization of the disubstituted succinates obtained by aldol condensation gave the paraconic acid natural products (-)-nephrosteranic acid (8) and (-)-roccellaric acid (9). The overall yield of the natural products 8 and 9 over four steps was 53% and 42%, respectively.
2. Catalytic enantioselective synthesis of naturally occurring butenolides via hetero-allylic alkylation and ring closing metathesis
Bin Mao, Koen Geurts, Martín Fañanás-Mastral, Anthoni W van Zijl, Stephen P Fletcher, Adriaan J Minnaard, Ben L Feringa Org Lett. 2011 Mar 4;13(5):948-51. doi: 10.1021/ol102994q. Epub 2011 Jan 26.
An efficient catalytic asymmetric synthesis of chiral γ-butenolides was developed based on the hetero-allylic asymmetric alkylation (h-AAA) in combination with ring closing metathesis (RCM). The synthetic potential of the h-AAA-RCM protocol was illustrated with the facile synthesis of (-)-whiskey lactone, (-)-cognac lactone, (-)-nephrosteranic acid, and (-)-roccellaric acid.
3. Enantioselective synthesis of paraconic acids
Rakeshwar B Chhor, Bernd Nosse, Sebastian Sörgel, Claudius Böhm, Michael Seitz, Oliver Reiser Chemistry. 2003 Jan 3;9(1):260-70. doi: 10.1002/chem.200390019.
The development of a new method for the enantioselective synthesis of disubstituted gamma-butyrolactones is reported. Based on this strategy, the total synthesis of three paraconic acids, that is (-)-roccellaric acid, (-)-nephrosteranic acid and (-)-protopraesorediosic acid, and the formal total synthesis of (-)-methylenolactocin and (-)-protolichesterinic acid is described, which are important because of their antibiotic and antitumor properties. Key steps of the synthesis are copper(I)-catalyzed asymmetric cyclopropanations of furans, highly diastereoselective Sakurai allylations, Lewis acid or Lewis base catalyzed retroaldol/lactonization cascades, and ruthenium(II)-catalyzed, intermolecular cross metathesis reactions.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
