兰州大学机构库 >化学化工学院
Synthetic studies towards the mannolides: Construction of the bowl-shaped B/C/D ring system
Wang, Kunkai; Xu, Zhezhe; Tan, Xiangchuang; Xie, Zhixiang
2020-12-04
Source PublicationTETRAHEDRON
ISSN0040-4020
Volume76Issue:49
AbstractThe bowl-shaped tricyclo[6.3.1.0(4)(,1)(2)]dodecane moiety is the core feature of cephalotane-type diterpenoids. As part of our efforts directed towards a total synthesis of mannolide B, the bowl-shaped tricyclo [6.3.1.0(4)(,1)(2)]dodecane skeleton, a common intermediate of cephalotane-type diterpenoids bearing up to five contiguous stereocenters including two quaternary carbon centers had been constructed. The synthetic strategy was enabled by an efficient application of oxidative dearomatization/intramolecular DielsAlder reaction to access highly functionalized building block with the tricyclo[5.2.2.0(2,6)]undecane unit from commercially available materials. The key feature was firstly used the cyclic olefins with secondary alcohol as dienophile for the intramolecular inverse electron demand Diels-Alder reaction. Further synthetic studies led to construct ring D by a regioselective Aldol reaction. (C) 2020 Elsevier Ltd. All rights reserved.
KeywordCephalotane-type diterpenoids Mannolides Oxidative dearomatization Intramolecular Diels-Alder reaction Aldol reaction
DOI10.1016/j.tet.2020.131629
Indexed BySCIE
Language英语
Funding ProjectNNSFC[21672088][21772079][21971096] ; Natural Science Foundation of Gansu Province[18JR4RA003]
WOS Research AreaChemistry
WOS SubjectChemistry, Organic
WOS IDWOS:000590766600003
PublisherPERGAMON-ELSEVIER SCIENCE LTD
Citation statistics
Cited Times:2[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.lzu.edu.cn/handle/262010/442427
Collection化学化工学院
Corresponding AuthorXie, Zhixiang
AffiliationLanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, 222 Tianshui South Rd, Lanzhou 730000, Peoples R China
First Author AffilicationCollege of Chemistry and Chemical Engineering
Corresponding Author AffilicationCollege of Chemistry and Chemical Engineering
Recommended Citation
GB/T 7714
Wang, Kunkai,Xu, Zhezhe,Tan, Xiangchuang,et al. Synthetic studies towards the mannolides: Construction of the bowl-shaped B/C/D ring system[J]. TETRAHEDRON,2020,76(49).
APA Wang, Kunkai,Xu, Zhezhe,Tan, Xiangchuang,&Xie, Zhixiang.(2020).Synthetic studies towards the mannolides: Construction of the bowl-shaped B/C/D ring system.TETRAHEDRON,76(49).
MLA Wang, Kunkai,et al."Synthetic studies towards the mannolides: Construction of the bowl-shaped B/C/D ring system".TETRAHEDRON 76.49(2020).
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