A modified total synthesis of cystothiazole A

A modified total synthesis of cystothiazole A

导出

摘要 A modified total synthesis of cystothiazole A is described. In this synthetic strategy, a one-step transformation of acylated oxazolidinone to β-ketoester has been successfully applied, thus making the synthetic route more efficient. This method may also be potentially applied in synthesis of other related β-substituted-β-methoxyl acrylates (bb-MOAs). A modified total synthesis of cystothiazole A is described. In this synthetic strategy, a one-step transformation of acylated oxazolidinone to β-ketoester has been successfully applied, thus making the synthetic route more efficient. This method may also be potentially applied in synthesis of other related β-substituted-β-methoxyl acrylates (bb-MOAs).

作者 YueXia Bai JiLai Bao Jun Ren ZhongWen Wang

机构地区 State Key Laboratory of Elemento-Organic Chemistry

出处《Science China Chemistry》 SCIE EI CAS 2009年第9期1345-1352,共8页 中国科学（化学英文版）

基金 Supported by the National Natural Science Foundation of China (Grant Nos. 20572045, 20542003 & 20421202) National Key Project of Scientific and Technical Supporting Programs (Grant No. 2006BAE01A01-5) Ministry of Education of China (Grant No. RFDF20070055022 and RSF [2005]383)

关键词 cystothiazole A &#946 -methoxyl acrylate Claisen condensation ALDOL total synthesis cystothiazole A β-methoxyl acrylate Claisen condensation Aldol total synthesis

分类号 O626 [理学—有机化学]

引文网络
相关文献

参考文献64

1Wessel H P,Lversen T,Bundle D R.Acid-catalysed benzylation and allylation by alkyl trichloroacetimidates. Journal of the Chemical Society Perkin Transactions 2 Physical Organic Chemistry . 1985
2Kwon S J,Ko S Y.Orthogonally protected, enantiopure syn-2- amino-1,3,4-butanetriol: A general building block for syn-amino alcohols. Journal of Organic Chemistry . 2001
3Wang X J,Chen L G,Li Y.Synthesis of methyl 2-(1-tert-butoxycar- bonylaminoethyl)thiazole-4-carboxylate. Chinese Journal of Organic Chemistry . 2004
4Sibi M P,Rutherford D,Sharma R.A new electrophilic alaninol synthon: A general route to oxazolidinones of D or (R)-2-amino al- cohols from L-serine. Journal of the Chemical Society Perkin Transactions 2 Physical Organic Chemistry . 1994
5Falb E,Bechor Y,Hassner A,Albeck A,Gottlib H E.IOOC Route to substituted chiral pyrrolidines: Potential glycosidase inhibitors. Journal of Organic Chemistry . 1999
6Sauter H,Steglich W,Anke T.Strobilurins: Evolution of a new class of active substances. Angewandte Chemie International Edition . 1999
7Anke T,Oberwinkler F,Steglic W,Hofle G.The strobilurins ―New antifungal antibiotics from the basidiomycete strobilurus tenacellus (Pers. ex Fr.) sing. Journal of Antibiotics . 1977
8Anke T,Schramm G,Schwalge B,Steffan B,Steglich W.Antibiotika aus basidiomyceten, XX Synthese von strobilurin A und revision der stereochemie der natürlichen strobilurine. Liebigs Annalen and Chemistry . 1984
9Anke T,Hecht H J,Schramm G,Steglich W.Antibiotics from basidiomycetes. IX Oudemansin, an antifungal antibiotic from oude- mansiella mucida (Schrader ex Fr.) hoehnel (agaricales). Journal of Antibiotics . 1979
10Sasse F,Leibold T,Kunze B,H?fle G,Reichenbach H.Cyrmenins, new β-methoxyacrylate inhibitors of the electron transport produc- tion, isolation, physico-chemical and biological properties. J Anti- biot . 2003

1于笑寒.乙酰丙酮的合成[J].山东化工,2016,45(24):8-9. 被引量：1
2柏月霞,鲍吉来,任军,王忠文.Cystothiazole A的改进全合成[J].中国科学（B辑）,2009(9):984-984.
3ZHANG Yang,HUANG Jie,SONG Ji-Rong,REN Ying-Hui,XU Kang-Zhen.Synthesis and Crystal Structure of 4-(4,6-Dimethoxylpyrimidin-2-yl)-3-thiourea Carboxylic Acid Ethyl Ester[J].Chinese Journal of Structural Chemistry,2008,27(2):195-199.
4Lun Zu LIU,Guo Wei LI,Xing Zhong ZENG,Ao ZHANNG,Xiao Dong SHI,Zhong Biao ZHANG (Institute of elemento-Organic Chemistry, Nankai University, Tianjian, 30071).NEW SYNTHETIC ROUTE TO ALKOXYPHOSPHORNES[J].Chinese Chemical Letters,1994,5(9):725-726.
5Zuo Sheng LIU ,Jiong LAN,Li Zeng PENG ,Yu Lin LI,Ya Cheng XING,Wen CEN (National Laboratory of Applied Organic Chemistry and Institute of Organic Chemistry.Lanzhou University Lanzhou 730000Department of Chemistry, Qingdao University. Qingdao 266071).Highly Stereoselective Synthesis of (E, E)-3,7-Dimethyl-2,6-decadiene-1,10-diol[J].Chinese Chemical Letters,1999,10(7):547-548.
6Jian Jun ZHAI,Wei YING,Fan Zhi ZHA0,Yao Zu CHEN(National Laboratory of Applied Organic Chemistry at Lanzhou University, Lanzhou 730000).Detection of Claisen Rearrangement Occurring in Allyl Phenyl Ether by in situ GC/MS[J].Chinese Chemical Letters,1998,9(4):381-384.
7王先恒.无溶剂的Claisen和Cannizzaro反应[J].中国医药工业杂志,2002,33(12):607-607.
8唐作华,周红平,孙泽民,鄢国森,田安民.Claisen重排反应的量子化学研究[J].Chinese Journal of Chemical Physics,1994,7(3):221-226.
9Chuan Zhou Tao,Wei Wei Lu,Ji You Sun.Copper-catalyzed synthesis of phenols from aryl halides and 4-methoxylbenzyl alcohol[J].Chinese Chemical Letters,2009,20(10):1170-1174. 被引量：1
10黄筱玲,曲凡歧,胡建华,姜风超.含［2，2］对环番基的1，3－丁二酮及其金属螯合物的合成[J].武汉大学学报（自然科学版）,1994,40(1):67-71.

Science China Chemistry

2009年第9期

浏览历史

内容加载中请稍等...

A modified total synthesis of cystothiazole A

参考文献64

相关作者

相关机构

相关主题

浏览历史