Kibdelone C

* Please be kindly noted products are not for therapeutic use. We do not sell to patients.

Kibdelone C
Category Bioactive by-products
Catalog number BBF-04263
CAS 934464-79-6
Molecular Weight 585.99
Molecular Formula C29H28ClNO10
Purity >95% by HPLC

Online Inquiry

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.

Recommended Products

Bio Calculators

Stock concentration: *
Desired final volume: *
Desired concentration: *

L

* 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
g/mol
g

Recently viewed products

Online Inquiry

Verification code

Copyright © 2025 BOC Sciences. All rights reserved.

cartIcon
0
Inquiry Basket

No data available, please add!

Delete selectedGo to checkout

We use cookies to understand how you use our site and to improve the overall user experience. This includes personalizing content and advertising. Read our Privacy Policy

Accept Cookies
x