Cladospolide A
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-00352 |
| CAS | 77663-54-8 |
| Molecular Weight | 228.28 |
| Molecular Formula | C12H20O4 |
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Description
It is produced by the strain of Cladosporium sp. FT-0012. Cladospolide A has little antibacterial activity.
Specification
| Synonyms | (-)-Cladospolide A; Oxacyclododec-3-en-2-one, 5,6-dihydroxy-12-methyl-, (3E,5R,6S,12R)- |
| IUPAC Name | (3E,5R,6S,12R)-5,6-dihydroxy-12-methyl-1-oxacyclododec-3-en-2-one |
| Canonical SMILES | CC1CCCCCC(C(C=CC(=O)O1)O)O |
| InChI | InChI=1S/C12H20O4/c1-9-5-3-2-4-6-10(13)11(14)7-8-12(15)16-9/h7-11,13-14H,2-6H2,1H3/b8-7+/t9-,10+,11-/m1/s1 |
| InChI Key | PLHJPQNLCWFPFY-OUZGJDHNSA-N |
Properties
| Appearance | White Powder |
Reference Reading
1. A chemoenzymatic total synthesis of the phytotoxic undecenolide (-)-cladospolide A
Martin G Banwell, David T J Loong Org Biomol Chem. 2004 Jul 21;2(14):2050-60. doi: 10.1039/b401829j. Epub 2004 Jun 23.
An eleven-step synthesis of the title compound (1) from biocatalytically-derived and enantiomerically pure 'building blocks' alcohol (R)-(-)-9 and ester 13 is described. Attempts to construct the twelve-membered lactone ring of cladospolide A in a direct manner by using a ring-closing metathesis (RCM) reaction failed. However, a ten-membered lactone 19, could be constructed by such means and this was then subject to a two-carbon homologation sequence involving, inter alia, Wadsworth-Horner-Emmons and Yamaguchi lactonisation reactions in the closing stages of the synthesis. The impact of substituent stereochemistries and protecting groups on the RCM reaction leading to various ten-membered lactones is also described.
2. A flexible and unified strategy for syntheses of cladospolides A, B, C, and iso-cladospolide B
Debjani Si, Narayana M Sekar, Krishna P Kaliappan Org Biomol Chem. 2011 Oct 21;9(20):6988-97. doi: 10.1039/c1ob05787a. Epub 2011 Aug 18.
A simple, efficient and flexible strategy for the syntheses of cladospolides A-C and iso-cladospolide B is reported here. This strategy involves Julia-Kocienski olefination and Yamaguchi macrolactonization as key steps, starting from either d-ribose or suitable tartaric acid esters. Although our initial efforts towards cladospolide A involving a ring closing metathetic approach were not successful, changing the mode of ring closure and the use of Julia-Kocienski olefination for the construction of the key intermediate solved this issue and paved the way for the completion of total syntheses of this class of natural products.
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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 ╳
