Gregatin B

Gregatin B

Names
IUPAC name Methyl (5R)-5-[(1E,3E)-hexa-1,3-dienyl]-2,5-dimethyl-4-oxofuran-3-carboxylate [1]
Identifiers
CAS Number	58801-71-1  Y
3D model (JSmol)	Interactive image
ChemSpider	28288843
PubChem CID	53304446
InChI InChI=1S/C14H18O4/c1-5-6-7-8-9-14(3)12(15)11(10(2)18-14)13(16)17-4/h6-9H,5H2,1-4H3/b7-6+,9-8+/t14-/m1/s1 Key: BNZPIQOOHVBONM-PAMVGZKNSA-N
SMILES CC/C=C/C=C/[C@@]1(C(=O)C(=C(O1)C)C(=O)OC)C
Properties
Chemical formula	C14H18O4
Molar mass	250.294 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Gregatin B is a metabolite of the fungi Cephalosporium gregatum and Aspergillus panamensis with the molecular formula C₁₄H₁₈O₄ ^{[2] [3]} Gregatin B is a weak antibiotic. ^{[4] [3]} Gregatin B was discovered in 1982 ^[3] and has been the subject of total synthesis. ^{[5] [6]}

References

1. "Gregatin B". Pubchem.ncbi.NLM.nih.gov.
2. Durbin, R. (2 December 2012). Toxins in Plant Disease. Elsevier. p. 410. ISBN   978-0-323-14704-0.
3. Buckingham, John (1987). Dictionary of Organic Compounds. Taylor & Francis. p. 367. ISBN   978-0-412-17050-8.
4. Bycroft, Barrie W.; Payne, David J. (9 August 2013). Dictionary of Antibiotics and Related Substances: with CD-ROM, Second Edition. CRC Press. p. 892. ISBN   978-1-4822-8215-3.
5. "Gregatin B | Chemical Substance Information | J-GLOBAL". Jglobal.JST.go.jp.
6. Kusakabe, Taichi; Kawai, Yasuko; Kato, Keisuke (4 October 2013). "Total Synthesis of (+)-Gregatin B and E". Organic Letters. 15 (19): 5102–5105. doi:10.1021/ol402472q. PMID   24066736.

Further reading

• Wijeratne, E. M. Kithsiri; Xu, Yaming; Arnold, A. Elizabeth; Gunatilaka, A. A. Leslie (January 2015). "Pulvinulin A, Graminin C, and cis-Gregatin B – New Natural Furanones from Pulvinula sp. 11120, a Fungal Endophyte of Cupressus arizonica". Natural Product Communications. 10 (1): 1934578X1501000. doi: 10.1177/1934578x1501000127 . ISSN   1934-578X. S2CID   39340804.
• Burghart-Stoll, H; Brückner, R (20 May 2011). "A serendipitous synthesis of (+)-gregatin B, second structure revisions of the aspertetronins, gregatins, and graminin A, structure revision of the penicilliols". Organic Letters. 13 (10): 2730–3. doi:10.1021/ol2008318. PMID   21526752.
• Peberdy, John F. (11 November 2013). Penicillium and Acremonium. Springer Science & Business Media. p. 222. ISBN   978-1-4899-1986-1.