DICP OpenIR
Enantioselective Total Syntheses of Kuwanon X, Kuwanon Y, and Kuwanol A
Gao, Lei1,2,3; Han, Jianguang3; Lei, Xiaoguang1,2,3,4,5
Source PublicationORGANIC LETTERS
2016-02-05
ISSN1523-7060
DOI10.1021/acs.orglett.5b03285
Volume18Issue:3Pages:360-363
Indexed BySCI
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Organic
WOS Research AreaChemistry
WOS KeywordDIELS-ALDER REACTION ; CULTIVATED MULBERRY TREE ; MORUS-LHOU KOIDZ ; STILBENE DERIVATIVES ; NATURAL-PRODUCTS ; LEWIS-ACID ; STEM BARK ; ALBA L ; ADDUCTS ; CATALYSIS
AbstractThe first enantioselective total syntheses of (-)-kuwanon X, (+)-kuwanon Y, and (+)-kuwanol A have been accomplished by using asymmetric Diels-Alder cyclo-addition promoted by chiral VANOL or VAPOL/boron Lewis acid. The biosynthesis-inspired asymmetric Diels-Alder cyclo-addition shows high exo selectivity (exo/endo = 13/1), which was unprecedented in the previous total syntheses of related prenylflavonoid Diels-Alder natural products. An acid catalyzed intramolecular ketalization process enabled a biomimetic transformation to construct the polycyclic skeleton of kuwanol A efficiently.
Language英语
WOS IDWOS:000369771800005
PublisherAMER CHEMICAL SOC
Citation statistics
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/171163
Collection中国科学院大连化学物理研究所
Corresponding AuthorLei, Xiaoguang
Affiliation1.Peking Union Med Coll, Grad Sch, Beijing 100730, Peoples R China
2.Chinese Acad Med Sci, Beijing 100730, Peoples R China
3.NIBS, Beijing 102206, Peoples R China
4.Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Beijing Natl Lab Mol Sci,Minist Educ, Coll Chem & Mol Engn,Synthet & Funct Biomol Ctr,D, Beijing 100871, Peoples R China
5.Peking Univ, Peking Tsinghua Ctr Life Sci, Beijing 100871, Peoples R China
Recommended Citation
GB/T 7714
Gao, Lei,Han, Jianguang,Lei, Xiaoguang. Enantioselective Total Syntheses of Kuwanon X, Kuwanon Y, and Kuwanol A[J]. ORGANIC LETTERS,2016,18(3):360-363.
APA Gao, Lei,Han, Jianguang,&Lei, Xiaoguang.(2016).Enantioselective Total Syntheses of Kuwanon X, Kuwanon Y, and Kuwanol A.ORGANIC LETTERS,18(3),360-363.
MLA Gao, Lei,et al."Enantioselective Total Syntheses of Kuwanon X, Kuwanon Y, and Kuwanol A".ORGANIC LETTERS 18.3(2016):360-363.
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