Reveromycin B
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| Category | Antibiotics |
| Catalog number | BBF-04176 |
| CAS | 144860-68-4 |
| Molecular Weight | 660.79 |
| Molecular Formula | C36H52O11 |
| Purity | >98% by HPLC |
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Description
Reveromycin B is a polyketide antibiotic isolated from Streptomyces, which can inhibit mitotic activity.
Specification
| Synonyms | BDBM50217842; ZINC49871994 |
| Storage | Store at -20°C |
| IUPAC Name | (2E,4S,5S,6E,8E)-10-[(2R,5S,8S,9R)-2-butyl-2-[(1S,2E,4E)-5-carboxy-1-(3-carboxypropanoyloxy)-4-methylpenta-2,4-dienyl]-8-methyl-1,10-dioxaspiro[4.5]decan-9-yl]-5-hydroxy-4,8-dimethyldeca-2,6,8-trienoic acid |
| Canonical SMILES | CCCCC1(CCC2(O1)CCC(C(O2)CC=C(C)C=CC(C(C)C=CC(=O)O)O)C)C(C=CC(=CC(=O)O)C)OC(=O)CCC(=O)O |
| InChI | InChI=1S/C36H52O11/c1-6-7-19-35(30(14-10-25(3)23-33(42)43)45-34(44)17-16-32(40)41)21-22-36(47-35)20-18-27(5)29(46-36)13-9-24(2)8-12-28(37)26(4)11-15-31(38)39/h8-12,14-15,23,26-30,37H,6-7,13,16-22H2,1-5H3,(H,38,39)(H,40,41)(H,42,43)/b12-8+,14-10+,15-11+,24-9+,25-23+/t26-,27-,28-,29+,30-,35+,36-/m0/s1 |
| InChI Key | XVFQIVPMOPJEIO-OXVOKJAASA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | Tan Lyophilisate |
| Boiling Point | 849.0±65.0°C at 760 mmHg |
| Density | 1.2±0.1 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF, DMSO |
Reference Reading
1.Stereoselective total synthesis of reveromycin B and C19-epi-reveromycin B.
Drouet KE1, Theodorakis EA. Chemistry. 2000 Jun 2;6(11):1987-2001.
Our studies toward the total synthesis of the reveromycin family of natural products are described herein. Our synthetic approach is efficient, stereocontrolled, and convergent and has resulted in the first synthesis of reveromycin B (4) and C19-epi-reveromycin B (55). Key steps of this successful strategy include: a modified Negishi coupling (construction of C7-C8 bond) and a Kishi-Nozaki reaction (construction of C19-C20 bond), which were employed in the attachment of the target side chains. The key building blocks for the total synthesis were thus defined as vinyl iodide 6, alkyne 7, and alkyne 8. Our synthesis illustrates the utility of the modified Negishi coupling for the construction of complex dienes, confirms the proposed stereochemistry of reveromycins and paves the way for the preparation of designed analogues for biological study.
2.Total synthesis of (-)-reveromycin B.
Cuzzupe AN1, Hutton CA, Lilly MJ, Mann RK, Rizzacasa MA, Zammit SC. Org Lett. 2000 Jan 27;2(2):191-4.
[structure: see text] The total synthesis of the epidermal growth factor inhibitor reveromycin B (2) is described. A novel, convergent, and stereoselective reaction sequence was utilized to construct the 5,6-spiroketal system 10 which was converted into the natural product 2 by a 16-step sequence.
3.Total synthesis of the epidermal growth factor inhibitor (-)-reveromycin B.
Cuzzupe AN1, Hutton CA, Lilly MJ, Mann RK, McRae KJ, Zammit SC, Rizzacasa MA. J Org Chem. 2001 Apr 6;66(7):2382-93.
The total synthesis of the epidermal growth factor inhibitor reveromycin B (2) in 25 linear steps from chiral methylene pyran 13 is described. The key steps involved an inverse electron demand hetero-Diels-Alder reaction between dienophile 13 and diene 12 to construct the 6,6-spiroketal 11 which upon oxidation with dimethyldioxirane and acid catalyzed rearrangement gave the 5,6-spiroketal aldehyde 9. Lithium acetylide addition followed by oxidation/reduction and protective group manipulation provided the reveromycin B spiroketal core 8 which was converted into the reveromycin A (1) derivative 6 in order to confirm the stereochemistry of the spiroketal segment. Introduction of the C1-C10 side chain began with sequential Wittig reactions to form the C8-C9 and C7-C6 bonds, and a tin mediated asymmetric aldol reaction installed the C4 and C5 stereocenters. The final key steps to the target molecule 2 involved a Stille coupling to introduce the C21-C22 bond, succinoylation, selective deprotection, oxidation, and Wittig condensation to form the final C2-C3 bond.
4.Total synthesis of reveromycin B.
Masuda T1, Osako K, Shimizu T, Nakata T. Org Lett. 1999 Sep 23;1(6):941-4.
[formula: see text] The stereoselective total synthesis of reveromycin B (2), a novel polyketide-type antibiotic, has been accomplished.
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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 ╳
