Coriolin
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| Category | Antibiotics |
| Catalog number | BBF-01058 |
| CAS | 33404-85-2 |
| Molecular Weight | 280.32 |
| Molecular Formula | C15H20O5 |
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Description
It is produced by the strain of Coriolus consors. It has anti-gram-positive bacteria, negative bacteria (weak), yeast and vaginal trichomoniasis activities. Coriolin of 5 μg/mL can inhibit the growth of yoshida sarcoma 61.6%. It had no inhibitory effect on Ehrlich ascites carcinoma in animals.
Specification
| Synonyms | (1aS,3S,7aR)-3bβ,4,5,6,6aβ,7-Hexahydro-4β,7α-dihydroxy-3aα,5,5-trimethylspiro[cyclopenta[4,5]pentaleno[1,6a-b]oxirene-3(3aH), 2'-oxiran]-2(1aH)-one; (3S,7aR)-3aα,5,5-Trimethyl-4β,7α-dihydroxy-1aβ,2,3bβ,4,5,6,6aβ,7-octahydrospiro[cyclopenta[4,5]pentaleno[1,6a-b]oxirene-3(3aH), 2'-oxirane-2-one; (-)-Coriolin; Coriolin A |
| IUPAC Name | (1R,2S,3S,6R,7R,8S,9S,11S)-2,6-dihydroxy-5,5,8-trimethylspiro[12-oxatetracyclo[6.4.0.01,11.03,7]dodecane-9,2'-oxirane]-10-one |
| Canonical SMILES | CC1(CC2C(C1O)C3(C4(CO4)C(=O)C5C3(C2O)O5)C)C |
| InChI | InChI=1S/C15H20O5/c1-12(2)4-6-7(9(12)17)13(3)14(5-19-14)10(18)11-15(13,20-11)8(6)16/h6-9,11,16-17H,4-5H2,1-3H3/t6-,7-,8-,9+,11+,13+,14-,15+/m0/s1 |
| InChI Key | OMAFWWAJLVYWPU-ZOEJUPFXSA-N |
Properties
| Appearance | Colorless Acicular Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; Neoplastics (Tumor); Parasites; Yeast |
| Melting Point | 175-166 °C (dec.) |
| Solubility | Soluble in Chloroform, Methanol, Ethyl Acetate |
Reference Reading
1. Applications of the squarate ester cascade to the expeditious synthesis of hypnophilin, coriolin, and ceratopicanol
Leo A Paquette, Feng Geng J Am Chem Soc. 2002 Aug 7;124(31):9199-203. doi: 10.1021/ja020474t.
The first applications of the squarate ester cascade to natural products synthesis have been realized. Only 10 laboratory steps mediate the conversion of diisopropyl squarate to (+/-)-hypnophilin (8). Key reactions include a combination of chlorination, reduction, dehydration, and oxidation maneuvers in the proper sequence. A penultimate precursor to 8 has previously been converted into coriolin (9), thereby allowing a formal synthesis of racemic 9 also to be claimed. A rather different strategy was employed to arrive at (+/-)-ceratopicanol (10). Of the seven steps involved, three consisted of the use of lithium in liquid ammonia. The three divergent synthetic objectives realized in these experiments involved (a) generation of an extended enolate anion and its regioselective C-methylation at the gamma-carbon; (b) unprecedented reductive cleavage of a beta-isopropoxy group in a 2,3-diisopropoxy-2-cyclopentenone setting; and (c) conventional conversion of an alpha-alkoxy ketone to the parent carbonyl system. Thus, the appreciable enhancement in structural complexity offered by the squarate cascade holds considerable potential for the concise synthesis of constitutionally intricate targets.
2. Hirsutane-type sesquiterpenes with uncommon modifications from three basidiomycetes
Johannes C Liermann, Anja Schüffler, Beate Wollinsky, Judith Birnbacher, Heinz Kolshorn, Timm Anke, Till Opatz J Org Chem. 2010 May 7;75(9):2955-61. doi: 10.1021/jo100202b.
From three basidiomycetes, Xeromphalina sp., Stereum sp., and Pleurocybella porrigens, six triquinane sesquiterpenes with unprecendented modifications and a rearranged sesquiterpene related to coriolin C have been isolated. Their isolation, structure elucidation, and biological evaluation are described.
3. Total Synthesis of (-)-Coriolin
Hajime Mizuno, Kei Domon, Keiichi Masuya, Keiji Tanino, Isao Kuwajima J Org Chem. 1999 Apr 16;64(8):2648-2656. doi: 10.1021/jo981478c.
An efficient synthetic method for (-)-coriolin has been developed on the basis of a [3+2] cycloaddition reaction of a 1-(methylthio)-2-siloxyallyl cationic species and vinylsulfides. An enantiomerically pure C-ring unit was prepared through optical resolution of five-membered allyl ester 6b using a lipase. The first [3+2] cycloaddition reaction of C-ring unit (S)-7 gave bicyclic ketones 8 and 9, which were easily converted into vinyl sulfide 11. Stereoselective construction of the A-ring was achieved by the second [3+2] cycloaddition reaction of the BC-ring unit. New methods for introduction of the oxygen functional groups to the triquinane skeleton were also developed for the last stages of the total synthesis. Thus, the C7 hydroxyl group was introduced by epoxidation of dienol silyl ether 17, and stereocontrolled construction of the spiro epoxide moiety was accomplished on the basis of a Darzens-type reaction.
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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 ╳
