Coriolin B
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| Category | Antibiotics |
| Catalog number | BBF-01059 |
| CAS | 33400-89-4 |
| Molecular Weight | 408.53 |
| Molecular Formula | C23H36O6 |
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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 | (1aR,3S,7aR)-1aβ,2,3bβ,4,5,6,6aβ,7-Octahydro-2α,7α-dihydroxy-4β-octanoyloxy-3aα,5,5-trimethylspiro[cyclopenta[4,5]pentaleno[1,6a-b]oxirene-3(3aH),2'-oxirane] |
| IUPAC Name | (1aR,2S,3S,3aR,3bR,4R,6aS,7S,7aR)-2,7-dihydroxy-3a,5,5-trimethyloctahydro-4H-spiro[cyclopenta[4,5]pentaleno[1,6a-b]oxirene-3,2'-oxiran]-4-yl octanoate |
Properties
| Appearance | Colorless Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; Neoplastics (Tumor); Parasites; Yeast |
| Melting Point | 215-216 °C (dec.) |
| Solubility | Soluble in Methanol, Acetone, Benzene, 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. Application of chiral cationic catalysts to several classical syntheses of racemic natural products transforms them into highly enantioselective pathways
Qi-Ying Hu, Gang Zhou, E J Corey J Am Chem Soc. 2004 Oct 27;126(42):13708-13. doi: 10.1021/ja046154m.
This paper describes the application of chiral oxazaborolidinium cations of type 2 to various enantioselective Diels-Alder reactions that have served as early key steps for the syntheses of complex natural products. In the original syntheses these Diels-Alder reactions produced racemic adducts and led to racemic target molecules unless a separation of enantiomers by classical resolution was employed. By use of chiral catalysts of type 2, chiral products were obtained directly from Diels-Alder reactions of achiral components in excellent yield and enantioselectivity and with the mechanistically predicted absolute configuration. As a result, a number of classical syntheses could be converted to enantioselective versions, including (1) cortisone/cortisol (Merck/Sarett), (2) dendrobine (Kende), (3) vitamin B(12) (Eschenmoser), (4) myrocin C (Chu-Moyer/Danishefsky), (5) coriolin and hirsutene (Mehta), (6) dendrobatid 251F (Aube), (7) silphinene (Ito), and (8) nicandrenone core (Stoltz/Corey).
3. Syntheses of corliolin, 1-deoxy-1-ketocoriolin and 1,8-dideoxy-1,8-diketocoriolin from coriolin B
Y Nishimura, Y Koyama, S Umezawa, T Takeuchi, M Ishizuka, H Umezawa J Antibiot (Tokyo). 1980 Apr;33(4):404-7. doi: 10.7164/antibiotics.33.404.
Hydrolysis of 5,8-di-O-tetrahydropyranyl-5-deoxo-5-hydroxycoriolin which was prepared from coriolin B, followed by oxidation of the hydroxy groups at C-5, or C-1 and C-5, or C-1, C-5 and C-8 afforded coriolin (2), 1-deoxy-1-ketocoriolin (3) and 1,8-dideoxy-1,8-diketocoriolin (4). All three ketones were found to have antitumor activity, whereas antibacterial activity was observed in 2 and 3 but not in 4.
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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 ╳
