Biscembranoids Formed from an alpha,beta-Unsaturated gamma-Lactone Ring as a Dienophile: Structure Revision and Establishment of Their Absolute Configurations Using Theoretical Calculations of Electronic Circular Dichroism Spectra

doi:10.1021/jo400069n

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	Biscembranoids Formed from an alpha,beta-Unsaturated gamma-Lactone Ring as a Dienophile: Structure Revision and Establishment of Their Absolute Configurations Using Theoretical Calculations of Electronic Circular Dichroism Spectra
	Jia, Rui 3,4; Kurtan, Tibor 1; Mandi, Attila 1; Yan, Xiao-Hong 3; Zhang, Wen 2; Guo, Yue-Wei3
刊名	JOURNAL OF ORGANIC CHEMISTRY
	2013-04-05
卷号	78 期号:7 页码:3113-3119
ISSN号	0022-3263
DOI	10.1021/jo400069n
文献子类	Article
英文摘要	Four new biscembranoids, bislatumlides C-F (1-4), were isolated from the Hainan soft coral Sarcophyton latum. Their structures were elucidated by detailed analysis of spectroscopic data and by comparison with reported data of related derivatives, leading to the structure revision of co-occurring bislatumlides A (5) and B (6) at the C-21 configuration. The absolute configurations of bislatumlides C and E (1 and 3) were determined by TDDFT calculations of their solution ECD spectra, allowing the configurational assignment of the related bislatumlides D and F (2 and 4) and A and B (5 and 6) as well. Bislatumlides A F (1-6) represent the only biscembranoids formed by the undescribed coupling pattern of Diels-Alder cycloaddition between the Delta(1(2)) double bond involving an alpha,beta-unsaturated gamma-lactone ring as a dienophile group and a trisubstituted conjugated Delta(21(34))/Delta(35(36))-butadiene moiety. An endo-cycloaddition gave 1, 2, 5, and 6, whereas an exo-cycloaddition produced 3 and 4. This is the first report of exo-addition dicembranoids from marine sources and from nature. Bislatumlides C and E (1, 3) could be used as ECD reference compounds in the determination of absolute configuration for related derivatives.
资助项目	National Marine "863" project[2013AA092902] ; National Marine "863" Project[2011AA09070102] ; Natural Science Foundation of China[21072204] ; Natural Science Foundation of China[21021063] ; STCSM International Cooperation Project between SIMM/China and ICB/Italy[10540702900] ; EU[00000000] ; SKLDR/SIMM Projects[SIMM1105KF-04] ; SKLDR/SIMM Projects[SIMM1106KF-11] ; CAS[KSCX2-YW-R-18] ; CAS[KSCX2-EW-R-15] ; Hungarian National Research Foundation[OTKA K105871] ; Hungarian National Research Foundation[K81701] ; National Information Infrastructure Development Institute[NIIFI 10038]
WOS关键词	CORAL SARCOPHYTON-TORTUOSUM ; PROBABLE BIOGENETIC PRECURSOR ; GORGONIAN DICHOTELLA-GEMMACEA ; METHYL SARCOPHYTOATE ; LOBOPHYTUM-PAUCIFLORUM ; MAGNETIC-RESONANCE ; CHEMICAL-SHIFTS ; GLAUCUM ; DITERPENOIDS ; HYDROCARBONS
WOS研究方向	Chemistry
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000317327800030
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/277660]
专题	天然药物化学研究室中科院受体结构与功能重点实验室新药研究国家重点实验室
通讯作者	Zhang, Wen
作者单位	1.Univ Debrecen, Dept Organ Chem, H-4010 Debrecen, Hungary; 2.Second Mil Med Univ, Sch Pharm, Res Ctr Marine Drugs, Shanghai 200433, Peoples R China 3.Chinese Acad Sci, Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China; 4.Shanghai Ocean Univ, Coll Fisheries & Life Sci, Water Environm & Ecol Engineer Res Ctr, Shanghai 201306, Peoples R China;
推荐引用方式 GB/T 7714	Jia, Rui,Kurtan, Tibor,Mandi, Attila,et al. Biscembranoids Formed from an alpha,beta-Unsaturated gamma-Lactone Ring as a Dienophile: Structure Revision and Establishment of Their Absolute Configurations Using Theoretical Calculations of Electronic Circular Dichroism Spectra[J]. JOURNAL OF ORGANIC CHEMISTRY,2013,78(7):3113-3119.
APA	Jia, Rui,Kurtan, Tibor,Mandi, Attila,Yan, Xiao-Hong,Zhang, Wen,&Guo, Yue-Wei.(2013).Biscembranoids Formed from an alpha,beta-Unsaturated gamma-Lactone Ring as a Dienophile: Structure Revision and Establishment of Their Absolute Configurations Using Theoretical Calculations of Electronic Circular Dichroism Spectra.JOURNAL OF ORGANIC CHEMISTRY,78(7),3113-3119.
MLA	Jia, Rui,et al."Biscembranoids Formed from an alpha,beta-Unsaturated gamma-Lactone Ring as a Dienophile: Structure Revision and Establishment of Their Absolute Configurations Using Theoretical Calculations of Electronic Circular Dichroism Spectra".JOURNAL OF ORGANIC CHEMISTRY 78.7(2013):3113-3119.