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Total Synthesis and Structure Revision of Palmarumycin B 6 .
- Source :
-
Journal of natural products [J Nat Prod] 2018 Aug 24; Vol. 81 (8), pp. 1803-1809. Date of Electronic Publication: 2018 Aug 13. - Publication Year :
- 2018
-
Abstract
- Palmarumycin B <subscript>6</subscript> and its regioisomer were synthesized via 7- and 13-step routes using 2-chlorophenol and 4-chlorophenyl methyl ether as the starting materials in overall yields of 2.7% and 12%, respectively. Their structures were characterized by <superscript>1</superscript> H and <superscript>13</superscript> C NMR, HRESIMS, and X-ray diffraction data. The structure of palmarumycin B <subscript>6</subscript> was revised as 6-chloropalmarumycin CP <subscript>17</subscript> . The bioassay results showed that the larvicidal activity of palmarumycin B <subscript>6</subscript> with an LC <subscript>50</subscript> value of 32.7 μM was significantly higher than that of its 8-chloro isomer, with an LC <subscript>50</subscript> value of 227.3 μM.
- Subjects :
- Animals
Insecticides chemical synthesis
Insecticides toxicity
Larva drug effects
Magnetic Resonance Spectroscopy
Molecular Structure
Naphthalenes chemical synthesis
Naphthalenes toxicity
Plant Extracts chemistry
Plant Leaves chemistry
Spectrometry, Mass, Electrospray Ionization
Spiro Compounds chemical synthesis
Spiro Compounds toxicity
Structure-Activity Relationship
X-Ray Diffraction
Insecticides chemistry
Naphthalenes chemistry
Spiro Compounds chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1520-6025
- Volume :
- 81
- Issue :
- 8
- Database :
- MEDLINE
- Journal :
- Journal of natural products
- Publication Type :
- Academic Journal
- Accession number :
- 30102534
- Full Text :
- https://doi.org/10.1021/acs.jnatprod.8b00258