Kibdelone C
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| Category | Bioactive by-products |
| Catalog number | BBF-04263 |
| CAS | 934464-79-6 |
| Molecular Weight | 585.99 |
| Molecular Formula | C29H28ClNO10 |
| Purity | >95% by HPLC |
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Description
It is the major analogue of a potent antitumour complex isolated from kibdelosporangium sp. MST-108465. It is structurally related to lysolipin and albofungin.
Specification
| Synonyms | (10S,12S,13R)-4-Chloro-6,7,10,11,12,13-hexahydro-5,10,12,13,15,16-hexahydroxy-8-methoxy-2-methyl-3-propyl-2H-[1]benzopyrano[2',3':6,7]naphth[2,1-g]isoquinoline-1,14-dione; (+)-Kibdelone C |
| Storage | Store at -20°C |
| IUPAC Name | (19S,21S,22R)-8-chloro-3,10,19,21,22,26-hexahydroxy-15-methoxy-6-methyl-7-propyl-17-oxa-6-azahexacyclo[12.12.0.02,11.04,9.016,25.018,23]hexacosa-1(14),2(11),3,7,9,15,18(23),25-octaene-5,24-dione |
| Canonical SMILES | CCCC1=C(C2=C(C3=C(C4=C(CC3)C(=C5C(=C4O)C(=O)C6=C(O5)C(CC(C6O)O)O)OC)C(=C2C(=O)N1C)O)O)Cl |
| InChI | InChI=1S/C29H28ClNO10/c1-4-5-11-20(30)16-17(29(39)31(11)2)23(36)14-9(21(16)34)6-7-10-15(14)24(37)19-25(38)18-22(35)12(32)8-13(33)27(18)41-28(19)26(10)40-3/h12-13,22,32-37H,4-8H2,1-3H3/t12-,13-,22-/m0/s1 |
| InChI Key | NEZGGHIIKFHZCZ-MZFXBISCSA-N |
| Source | Kibdelosporangium sp. |
Properties
| Appearance | Yellow Solid |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 968.8±65.0°C at 760 mmHg |
| Density | 1.71±0.1 g/cm3 at 20°C 760 mmHg |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO |
Reference Reading
1. Total synthesis and absolute stereochemical assignment of kibdelone C
John A Porco Jr, David L Sloman, Jeffrey W Bacon J Am Chem Soc . 2011 Jul 6;133(26):9952-5. doi: 10.1021/ja203642n.
Kibdelones are hexacyclic tetrahydroxanthones and potent anticancer agents isolated from an Australian microbe. Herein, we describe the synthesis of a chiral, nonracemic iodocyclohexene carboxylate EF ring fragment of the kibdelones employing an intramolecular iodo halo-Michael aldol reaction and its merger with an ABCD ring fragment to afford the congener kibdelone C.
2. Convergent Synthesis of Kibdelone C
Tao Xie, Yihua Dai, Yanfang Shen, Shuanhu Gao, Feixia Ma Org Lett . 2018 May 18;20(10):2872-2875. doi: 10.1021/acs.orglett.8b00901.
The synthesis of kibdelone C, a polycyclic natural xanthone isolated from a soil actinomycete, was achieved through a convergent approach. A 6π-electrocyclization was applied to construct the highly substituted dihydrophenanthrenol fragment (B-C-D ring). InBr3-promoted lactonization was employed to build the isocoumarin ring, which served as a common precursor for the formation of isoquinolinone ring (A-B ring). A key DMAP-mediated oxa-Michael/aldol cascade reaction was developed to install the tetrahydroxanthone fragment (E-F ring). This approach provides a new solution to prepare its derivatives and structurally related natural products.
3. Enantioselective Halolactonization Reactions using BINOL-Derived Bifunctional Catalysts: Methodology, Diversification, and Applications
J Caleb Hethcox, Christopher R Shugrue, Stephen F Martin, Daniel W Klosowski, Andrew D Pansick, James R Donald, Chao Fang, Daniel H Paull J Org Chem . 2018 Jun 1;83(11):5954-5968. doi: 10.1021/acs.joc.8b00490.
A general protocol is described for inducing enantioselective halolactonizations of unsaturated carboxylic acids using novel bifunctional organic catalysts derived from a chiral binaphthalene scaffold. Bromo- and iodolactonization reactions of diversely substituted, unsaturated carboxylic acids proceed with high degrees of enantioselectivity, regioselectivity, and diastereoselectivity. Notably, these BINOL-derived catalysts are the first to induce the bromo- and iodolactonizations of 5-alkyl-4( Z)-olefinic acids via 5- exo mode cyclizations to give lactones in which new carbon-halogen bonds are created at a stereogenic center with high diastereo- and enantioselectivities. Iodolactonizations of 6-substituted-5( Z)-olefinic acids also occur via 6- exo cyclizations to provide δ-lactones with excellent enantioselectivities. Several notable applications of this halolactonization methodology were developed for desymmetrization, kinetic resolution, and epoxidation of Z-alkenes. The utility of these reactions is demonstrated by their application to a synthesis of precursors of the F-ring subunit of kibdelone C and to the shortest catalytic, enantioselective synthesis of (+)-disparlure reported to date.
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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 ╳
