Bisabosqual A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00153 |
| CAS | |
| Molecular Weight | 384.46 |
| Molecular Formula | C23H28O5 |
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Description
Bisabosqual A is a squalene synthase inhibitor produced by Stach-ybotrys sp. RF-7260. Bisabosqual A has broad-spectrum antifungal activity.
Specification
| Synonyms | (3S,3aR,9S,9aR,9bS)-2,3,3a,9,9a,9b-Hexahydro-3-hydroxy-3,9-dimethyl-9-(4-methyl-3-pentenyl)-1H-benzofuro[4,3,2-cde][1]benzopyran-5,6-dicarbaldehyde |
| IUPAC Name | (7S,8R,11S,12R,13S)-11-hydroxy-7,11-dimethyl-7-(4-methylpent-3-enyl)-6,15-dioxatetracyclo[10.2.1.05,14.08,13]pentadeca-1,3,5(14)-triene-2,3-dicarbaldehyde |
| Canonical SMILES | CC(=CCCC1(C2CCC(C3C2C4=C(O1)C=C(C(=C4O3)C=O)C=O)(C)O)C)C |
| InChI | InChI=1S/C23H28O5/c1-13(2)6-5-8-23(4)16-7-9-22(3,26)21-18(16)19-17(28-23)10-14(11-24)15(12-25)20(19)27-21/h6,10-12,16,18,21,26H,5,7-9H2,1-4H3/t16-,18+,21-,22+,23+/m1/s1 |
| InChI Key | JBVANMOFCVQYLP-MQRVUQIVSA-N |
Properties
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 519.9±50.0 °C at 760 mmHg |
| Density | 1.2±0.1 g/cm3 |
Reference Reading
1. Total synthesis of (±)-bisabosqual A
Christopher W am Ende, Zhou Zhou, Kathlyn A Parker J Am Chem Soc. 2013 Jan 16;135(2):582-5. doi: 10.1021/ja3108577. Epub 2012 Dec 28.
The synthesis of the novel squalene synthase inhibitor, bisabosqual A, was completed in 14 steps (longest linear sequence) from commercially available starting materials. The doubly convergent route employs a tandem 5-exo, 6-exo radical cyclization as the key step. This reaction assembles the fully functionalized tetracyclic core and introduces three stereogenic centers. Other effective transformations are the regioselective deoxygenation of an advanced enone intermediate and the chemo- and diastereoselective addition of trimethylaluminum to a ketone in the presence of esters.
2. Synthetic approaches to natural products containing 2,3-dihydrobenzofuran skeleton
Zhuang Chen, Mallesham Pitchakuntla, Yanxing Jia Nat Prod Rep. 2019 Apr 17;36(4):666-690. doi: 10.1039/c8np00072g.
Covering: 2000 to 2018 Natural products containing the 2,3-dihydrobenzofuran (2,3-DHB) skeleton have been the focus of a substantial number of synthetic studies since 2000. Herein, we review the total syntheses of decursivine, serotobenine, lithospermic acid, linderol A, bisabosqual A, pterocarpans, conocarpan, heliannuols, and some resveratrol oligomers, with emphasis on the synthetic strategies employed.
3. Synthesis of the alkenyl-substituted tetracyclic core of the bisabosquals
Jingye Zhou, Mercedes Lobera, Bobbianna J Neubert-Langille, Barry B Snider Tetrahedron. 2007 Oct 1;63(10):10018-10024. doi: 10.1016/j.tet.2007.07.033.
HCl-catalyzed deprotection and cyclization of benzylic alcohol 15 cleanly provided tricycle 16 by a cis-selective intramolecular Diels-Alder reaction. Acetylation of the phenol, bis epoxidation, and base-catalyzed hydrolysis and cyclization afforded tetracycle 19 with the bisabosqual skeleton, but the wrong stereochemistry at the tertiary alcohol. Selective dehydration of the tertiary alcohol to form the exocyclic alkene, ozonolysis, reductive deoxygenation of the side chain epoxide, and addition of MeMgBr to the ketone from the less hindered face gave tertiary alcohol 24 with the tetracyclic core of bisabosqual A (1).
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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 ╳
