A facile and highly atom-economic approach to biaryl-containing medium-ring bislactones

被引:18
作者
Wu, Dongdong [1 ]
Wang, Lei [1 ]
Xu, Kai [1 ]
Song, Jia [1 ]
Fun, Hoong-Kun [2 ]
Xu, Jianhua [1 ]
Zhang, Yan [1 ]
机构
[1] Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Analyt Chem Life Sci, Nanjing 210093, Jiangsu, Peoples R China
[2] Univ Sains Malaysia, Sch Phys, Xray Crystallog Unit, Usm Penang 11800, Malaysia
基金
中国国家自然科学基金;
关键词
SINGLET OXYGEN; ORGANOCUPRATE OXIDATION; NATURAL-PRODUCTS; O-QUINONES; PHOTOOXYGENATION; CHEMISTRY; SYSTEMS; REGIO;
D O I
10.1039/c2cc16492b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Starting from readily available phenanthrenequinone and alkenes, biaryl containing medium-ring bislactones could be easily prepared through sequential photocycloaddition-photooxidation reactions with good yields and diastereoselectivity.
引用
收藏
页码:1168 / 1170
页数:3
相关论文
共 35 条
[1]  
[Anonymous], 1995, ACTIVE OXYGEN CHEM
[2]   Photochemical Reactions as Key Steps in Natural Product Synthesis [J].
Bach, Thorsten ;
Hehn, Joerg P. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (05) :1000-1045
[3]   Electron transfer and singlet oxygen mechanisms in the photooxygenation of dibutyl sulfide and thioanisole in MeCN sensitized by N-methylquinolinium tetrafluoborate and 9,10-dicyanoanthracene.: The probable involvement of a thiadioxirane intermediate in electron transfer photooxygenations [J].
Baciocchi, E ;
Del Giacco, T ;
Elisei, F ;
Gerini, MF ;
Guerra, M ;
Lapi, A ;
Liberali, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (52) :16444-16454
[4]  
Boye O., 1992, ALKALOIDS, V41, P125
[5]   Atroposelective Total Synthesis of Axially Chiral Biaryl Natural Products [J].
Bringmann, Gerhard ;
Gulder, Tanja ;
Gulder, Tobias A. M. ;
Breuning, Matthias .
CHEMICAL REVIEWS, 2011, 111 (02) :563-639
[6]   Chemistry of trans-Resveratrol with Singlet Oxygen: [2+2] Addition, [4+2] Addition, and Formation of the Phytoalexin Moracin M [J].
Celaje, Jeff A. ;
Zhang, Dong ;
Guerrero, Angela M. ;
Selke, Matthias .
ORGANIC LETTERS, 2011, 13 (18) :4846-4849
[7]   SENSITIZED PHOTOOXYGENATION .1. REACTION OF SINGLET OXYGEN WITH 3,4-DIHYDRO-6-METHYL-2H-PYRAN-5-CARBOXYLIC ACID ETHYL-ESTER - ISOLATION OF HYDROPEROXIDES AND EVIDENCE OF THE TRANSFORMATION OF ONE OF THEM TO DIOXETANE [J].
CHAN, YY ;
ZHU, C ;
LEUNG, HK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (18) :5274-5275
[8]   Photoaddition reactions of 1,2-diketones with silyl ketene acetals.: Formation of β-hydroxy-γ-ketoesters [J].
Cho, Dae Won ;
Lee, Hyang-Yeol ;
Oh, Sun Wha ;
Choi, Jung Hei ;
Park, Hea Jung ;
Mariano, Patrick S. ;
Yoon, Ung Chan .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (12) :4539-4547
[9]   MECHANISM OF PHENANTHRENEQUINONE PHOTOCYCLOADDITION TO OLEFINS [J].
CHOW, YL ;
JOSEPH, TC .
CHEMICAL COMMUNICATIONS, 1968, (11) :604-&
[10]   SINGLET OXYGEN DIMOL-SENSITIZED LUMINESCENCE FROM THERMALLY GENERATED SINGLET OXYGEN [J].
FU, YL ;
KRASNOVSKY, AA ;
FOOTE, CS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :10282-10285