Dihydrocompactin
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01400 |
| CAS | 78366-44-6 |
| Molecular Weight | 392.53 |
| Molecular Formula | C23H36O5 |
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Description
Dihydrocompactin is produced by the strain of Penicillum citrinum (SANK 18767). It has inhibitory effect on HMG-COA.
Specification
| Synonyms | 8-[2-(4-Hydroxy-6-oxooxan-2-yl)ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl 2-methylbutanoate |
| IUPAC Name | [(1S,4aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2S)-2-methylbutanoate |
| Canonical SMILES | CCC(C)C(=O)OC1CCCC2C1C(C(C=C2)C)CCC3CC(CC(=O)O3)O |
| InChI | InChI=1S/C23H36O5/c1-4-14(2)23(26)28-20-7-5-6-16-9-8-15(3)19(22(16)20)11-10-18-12-17(24)13-21(25)27-18/h8-9,14-20,22,24H,4-7,10-13H2,1-3H3/t14-,15?,16+,17+,18+,19?,20-,22?/m0/s1 |
| InChI Key | VXDSGTRNDFHIJB-QQPOVDNESA-N |
Properties
| Appearance | Oil |
Reference Reading
1. Remote asymmetric induction in an intramolecular ionic Diels-Alder reaction: application to the total synthesis of (+)-dihydrocompactin
Tarek Sammakia, Deidre M Johns, Ganghyeok Kim, Martin A Berliner J Am Chem Soc. 2005 May 11;127(18):6504-5. doi: 10.1021/ja043506g.
The total synthesis of (+)-dihydrocompactin via an intramolecular ionic Diels-Alder reaction that proceeds with remote stereocontrol is described. This reaction proceeds by an intermediate vinyl-oxocarbenium ion (6), the conformational constraints of which lead to the observed asymmetric induction. The sense of asymmetric induction appears contrasteric and is explained by the proposed reactive conformation shown in Figure 1.
2. Ru-Based Catechothiolate Complexes Bearing an Unsaturated NHC Ligand: Effective Cross-Metathesis Catalysts for Synthesis of ( Z)-α,β-Unsaturated Esters, Carboxylic Acids, and Primary, Secondary, and Weinreb Amides
Zhenxing Liu, Chaofan Xu, Juan Del Pozo, Sebastian Torker, Amir H Hoveyda J Am Chem Soc. 2019 May 1;141(17):7137-7146. doi: 10.1021/jacs.9b02318. Epub 2019 Apr 17.
Despite notable progress, olefin metathesis methods for preparation of ( Z)-α,β-unsaturated carbonyl compounds, applicable to the synthesis of a large variety of bioactive molecules, remain scarce. Especially desirable are transformations that can be promoted by ruthenium-based catalysts, as such entities would allow direct access to carboxylic esters and amides, or acids (in contrast to molybdenum- or tungsten-based alkylidenes). Here, we detail how, based on the mechanistic insight obtained through computational and experimental studies, a readily accessible ruthenium catechothiolate complex was found that may be used to generate many α,β-unsaturated carbonyl compounds in up to 81% yield and ≥98:2 Z/ E ratio. We show that through the use of a complex bearing an unsaturated N-heterocyclic carbene (NHC) ligand, for the first time, products derived from the more electron-deficient esters, acids, and Weinreb amides (vs primary or secondary amides) can be synthesized efficiently and with high stereochemical control. The importance of the new advance to synthesis of bioactive compounds is illustrated through two representative applications: an eight-step, 15% overall yield, and completely Z-selective route leading to an intermediate that may be used in synthesis of stagonolide E (vs 11 steps, 4% overall yield and 91% Z, previously), and a five-step, 25% overall yield sequence to access a precursor to dihydrocompactin (vs 13 steps and 5% overall yield, formerly).
3. Stereodivergent, Diels-Alder-initiated organocascades employing α,β-unsaturated acylammonium salts: scope, mechanism, and application
Mikail E Abbasov, Brandi M Hudson, Dean J Tantillo, Daniel Romo Chem Sci. 2017 Feb 1;8(2):1511-1524. doi: 10.1039/c6sc04273b. Epub 2016 Oct 21.
Chiral α,β-unsaturated acylammonium salts are novel dienophiles enabling enantioselective Diels-Alder-lactonization (DAL) organocascades leading to cis- and trans-fused, bicyclic γ- and δ-lactones from readily prepared dienes, commodity acid chlorides, and a chiral isothiourea organocatalyst under mild conditions. We describe extensions of stereodivergent DAL organocascades to other racemic dienes bearing pendant secondary and tertiary alcohols, and application to a formal synthesis of (+)-dihydrocompactin is described. A combined experimental and computational investigation of unsaturated acylammonium salt formation and the entire DAL organocascade pathway provide a rationalization of the effect of Brønsted base additives and enabled a controllable, diastereodivergent DAL process leading to a full complement of possible stereoisomeric products. Evaluation of free energy and enthalpy barriers in conjunction with experimentally observed temperature effects revealed that the DAL is a rare case of an entropy-controlled diastereoselective process. NMR analysis of diene alcohol-Brønsted base interactions and computational studies provide a plausible explanation of observed stabilization of exo transition-state structures through hydrogen-bonding effects.
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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 ╳
