Clavilactone A
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| Category | Antibiotics |
| Catalog number | BBF-00364 |
| CAS | |
| Molecular Weight | 276.28 |
| Molecular Formula | C15H16O5 |
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Description
Clavilactone A is produced by the strain of Clitocybe clavipes. It can inhibit the germination of seeds.
Specification
| IUPAC Name | (1S,4Z,13S,14S)-8,11-dihydroxy-15,17-dioxatetracyclo[11.2.2.01,14.07,12]heptadeca-4,7(12),9-trien-16-one |
| Canonical SMILES | C1CC23C(O2)C(C4=C(CC=C1)C(C=CC4O)O)OC3=O |
| InChI | InChI=1S/C15H16O5/c16-9-5-6-10(17)11-8(9)4-2-1-3-7-15-13(20-15)12(11)19-14(15)18/h1-2,5-6,9-10,12-13,16-17H,3-4,7H2/b2-1-/t9?,10?,12-,13-,15-/m0/s1 |
| InChI Key | MWDWCBKPYZJUOT-ZEMVOCFZSA-N |
Properties
| Appearance | Yellow Crystallineline |
| Melting Point | 176 °C |
Reference Reading
1. Total Synthesis of Clavilactones
Ken-Ichi Takao, Kento Mori, Kenya Kasuga, Ryuki Nanamiya, Ayumi Namba, Yuuki Fukushima, Ryuichi Nemoto, Takuma Mogi, Hiroyuki Yasui, Akihiro Ogura, Keisuke Yoshida, Kin-Ichi Tadano J Org Chem. 2018 Jul 6;83(13):7060-7075. doi: 10.1021/acs.joc.7b03268. Epub 2018 Feb 5.
Clavilactones A, B, and D are epidermal growth factor receptor tyrosine kinase inhibitors that were isolated from cultures of the fungus Clitocybe clavipes. Here, we report full details of the total synthesis of these clavilactones. A key feature of our synthetic approach is a ring-opening/ring-closing metathesis strategy that allows the concise transformation of a cyclobutenecarboxylate into a γ-butenolide. Coupled with enantioselective Ti/BINOL-catalyzed alkynylation of a multisubstituted benzaldehyde and ring-closing metathesis of a diene-bearing silylene acetal to construct the 10-membered carbocycle, this strategy enabled the total synthesis of the natural enantiomers (+)-clavilactone A and (-)-clavilactone B. In addition, the correct structure of clavilactone D was determined by the synthesis of two newly proposed structures. This research resulted in the asymmetric synthesis of the revised (+)-clavilactone D.
2. Total synthesis of (+)-clavilactone A and (-)-clavilactone B by ring-opening/ring-closing metathesis
Ken-ichi Takao, Ryuki Nanamiya, Yuuki Fukushima, Ayumi Namba, Keisuke Yoshida, Kin-ichi Tadano Org Lett. 2013 Nov 1;15(21):5582-5. doi: 10.1021/ol4027842. Epub 2013 Oct 22.
The enantioselective total synthesis of natural enantiomers of clavilactones A and B has been achieved. A key feature of the synthesis is the use of a ring-opening/ring-closing metathesis, which allows the one-pot transformation of a strained cyclobutenecarboxylate into a γ-butenolide.
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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 ╳
