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Multiple reactivities of dithranol towards 1-alkynyl Fischer carbene complexes (CO)(5)M=C(OEt)C CPh (M = Cr, W) - Efficient chemical synthesis of aromatic polyketides
Luo, Ning1; Yu, Zhengkun1,2
KeywordFischer Carbene Dithranol Multiple Reactivity Polyketides Polycarbene
Source PublicationJOURNAL OF ORGANOMETALLIC CHEMISTRY
2009-09-01
DOI10.1016/j.jorganchem.2009.05.029
Volume694Issue:19Pages:3058-3067
Indexed BySCI ; IC
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Inorganic & Nuclear ; Chemistry, Organic
WOS Research AreaChemistry
WOS KeywordH INSERTION ; PATHWAY ; CHROMIUM ; DEMETALATION ; ANTHRACENE
AbstractReactions of anti-psoriasis drug dithranol with 1-alkynyl Fischer carbene complexes (CO)(5)M =C(OEt)C CPh (M = Cr, W) were investigated under controlled conditions in which triethylamine-promoted C-addition, O-addition, electrophilic aromatic substitution, and cyclization consecutively occurred at up to five positions of dithranol. A remarkable solvent effect led to selective formation of polyphenolic organic and organometallic mono- and triscarbene complexes which were efficiently demetalated to the potentially bioactive aromatic polyketides with pyridine-N-oxide. All the organic and organometallic products were characterized by methods including X-ray single crystal structural determinations. These results have revealed the novel multiple reactivities of dithranol which might be associated to its clinical side effect, providing a new synthetic methodology to functionalize dithranol for medical purposes, and chemically synthesize aromatic polyketides. (C) 2009 Elsevier B. V. All rights reserved.
Language英语
WOS IDWOS:000268799500003
Citation statistics
Cited Times:4[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/141623
Collection中国科学院大连化学物理研究所
Affiliation1.Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Liaoning, Peoples R China
2.Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
Recommended Citation
GB/T 7714
Luo, Ning,Yu, Zhengkun. Multiple reactivities of dithranol towards 1-alkynyl Fischer carbene complexes (CO)(5)M=C(OEt)C CPh (M = Cr, W) - Efficient chemical synthesis of aromatic polyketides[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY,2009,694(19):3058-3067.
APA Luo, Ning,&Yu, Zhengkun.(2009).Multiple reactivities of dithranol towards 1-alkynyl Fischer carbene complexes (CO)(5)M=C(OEt)C CPh (M = Cr, W) - Efficient chemical synthesis of aromatic polyketides.JOURNAL OF ORGANOMETALLIC CHEMISTRY,694(19),3058-3067.
MLA Luo, Ning,et al."Multiple reactivities of dithranol towards 1-alkynyl Fischer carbene complexes (CO)(5)M=C(OEt)C CPh (M = Cr, W) - Efficient chemical synthesis of aromatic polyketides".JOURNAL OF ORGANOMETALLIC CHEMISTRY 694.19(2009):3058-3067.
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