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Crocacin C

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Category Enzyme inhibitors
Catalog number BBF-01081
CAS 237425-38-6
Molecular Weight 357.49
Molecular Formula C22H31NO3

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Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

It is produced by the strain of Chondromyces crocatus sp. Cm c3. It has anti-yeast and filamentous fungal activity. It can inhibit mouse fibroblasts L929 (MIC is 0.2 ng). In the microsomes of the calf's heart, it can interrupt the bc1 segment of electronic transmission, causes redshift of 569nm peak in cytochrome B reduction spectrum.

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Synonyms (+)-Crocacin C; (2E,4E,10E)(6S,7S,9S,8R)-7,9-Dimethoxy-3,6,8-trimethyl-11-phenylundeca-2,4,10-trienamide; 7,9-dimethoxy-3,6,8-trimethyl-11-phenyl-(2E,4E,6S,7S,8R,9S,10E)-2,4,10-undecatrienamide
IUPAC Name (2E,4E,6S,7S,8R,9S,10E)-7,9-dimethoxy-3,6,8-trimethyl-11-phenylundeca-2,4,10-trienamide
Canonical SMILES CC(C=CC(=CC(=O)N)C)C(C(C)C(C=CC1=CC=CC=C1)OC)OC
InChI InChI=1S/C22H31NO3/c1-16(15-21(23)24)11-12-17(2)22(26-5)18(3)20(25-4)14-13-19-9-7-6-8-10-19/h6-15,17-18,20,22H,1-5H3,(H2,23,24)/b12-11+,14-13+,16-15+/t17-,18+,20-,22-/m0/s1
InChI Key JCMQQWWEDGWMJB-ZAFMVVCLSA-N
Antibiotic Activity Spectrum Gram-positive bacteria; Fungi; Yeast
Melting Point 95-100 °C
Solubility Soluble in Methanol
1. Step-economic synthesis of (+)-crocacin C: a concise crotylboronation/[3,3]-sigmatropic rearrangement approach
Adele E Pasqua, Frank D Ferrari, Chris Hamman, Yanzhou Liu, James J Crawford, Rodolfo Marquez J Org Chem. 2012 Aug 17;77(16):6989-97. doi: 10.1021/jo301210f. Epub 2012 Aug 2.
The step-economic total synthesis of (+)-crocacin C has been achieved in 20% yield from commercially available starting materials. This approach requires the isolation of only 8 intermediates and can provide a reliable supply of (+)-crocacin C for the development of new antifungal and crop protection agents.
2. Synthesis of (+)-crocacin D and simplified bioactive analogues
Adele E Pasqua, Frank D Ferrari, James J Crawford, William G Whittingham, Rodolfo Marquez Bioorg Med Chem. 2015 Mar 1;23(5):1062-8. doi: 10.1016/j.bmc.2015.01.008. Epub 2015 Jan 10.
The total synthesis of (+)-crocacin D has been achieved in 15 steps (9 isolated intermediates) and 14% overall yield from commercially available starting materials and using (+)-crocacin C as a key intermediate. A number of simplified analogues and their biological activities are also reported.
3. Enantioselective synthesis of (+)-crocacin C. An example of a highly challenging mismatched double asymmetric δ-stannylcrotylboration reaction
Ming Chen, William R Roush Org Lett. 2012 Apr 6;14(7):1880-3. doi: 10.1021/ol300476f. Epub 2012 Mar 12.
A concise, enantioselective synthesis of (+)-crocacin C is described, featuring a highly diastereoselective mismatched double asymmetric δ-stannylcrotylboration of the stereochemically demanding chiral aldehyde 9 with the bifunctional crotylborane reagent (S)-E-10. The total synthesis of (+)-crocacin C was accomplished in seven steps (longest linear sequence) starting from commercially available precursors.

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