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Total Synthesis and Structure Revision of Palmarumycin B 6 .

Authors :
Liu X
Wang W
Zhao Y
Lai D
Zhou L
Liu Z
Wang M
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.

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