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Access to the 2H-Tetrahydro-4,6-dioxo-1,2-oxazine Ring System from Nitrone via a Tandem Nucleophilic Addition and Transesterification Reaction
Yang, Shaoqiang1; Liao, Daohong1; Tian, Xiaoqi1; Lei, Xiaoguang1,2,3
Source PublicationORGANIC LETTERS
2016-02-05
ISSN1523-7060
DOI10.1021/acs.orglett.5b03374
Volume18Issue:3Pages:376-379
Indexed BySCI
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Organic
WOS Research AreaChemistry
WOS KeywordDIELS-ALDER REACTION ; HETEROCYCLIC NATURAL-PRODUCTS ; DIASTEREOSELECTIVE ADDITION ; ASSISTED ALKYNYLATION ; ALDEHYDES ; DIENE ; HYDROXYLAMINES ; STREPTOMYCES ; ALCHIVEMYCIN ; DERIVATIVES
AbstractA general and efficient synthesis of the 2H-tetrahydro-4,6-dioxo-1,2-oxazine ring system through a tandem nucleophilic addition and transesterification reaction is described. The reaction is highly functional-group-tolerant and proceeds under mild conditions, affording the corresponding products in good to excellent yields. This method represents the first general synthetic route to access this heterocyclic scaffold, which exists in the complex natural products alchivemycin A and B with significant antibiotic activities.
Language英语
WOS IDWOS:000369771800009
PublisherAMER CHEMICAL SOC
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/321008/171187
Collection中国科学院大连化学物理研究所
Corresponding AuthorLei, Xiaoguang
Affiliation1.Tianjin Univ, Sch Pharmaceut Sci & Technol, Tianjin 300072, Peoples R China
2.Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Coll Chem & Mol Engn,Synthet & Funct Biomol Ctr, Beijing Natl Lab Mol Sci,Dept Chem Biol,Minist Ed, Beijing 100871, Peoples R China
3.Peking Univ, Ctr Life Sci, Beijing 100871, Peoples R China
Recommended Citation
GB/T 7714
Yang, Shaoqiang,Liao, Daohong,Tian, Xiaoqi,et al. Access to the 2H-Tetrahydro-4,6-dioxo-1,2-oxazine Ring System from Nitrone via a Tandem Nucleophilic Addition and Transesterification Reaction[J]. ORGANIC LETTERS,2016,18(3):376-379.
APA Yang, Shaoqiang,Liao, Daohong,Tian, Xiaoqi,&Lei, Xiaoguang.(2016).Access to the 2H-Tetrahydro-4,6-dioxo-1,2-oxazine Ring System from Nitrone via a Tandem Nucleophilic Addition and Transesterification Reaction.ORGANIC LETTERS,18(3),376-379.
MLA Yang, Shaoqiang,et al."Access to the 2H-Tetrahydro-4,6-dioxo-1,2-oxazine Ring System from Nitrone via a Tandem Nucleophilic Addition and Transesterification Reaction".ORGANIC LETTERS 18.3(2016):376-379.
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