Total Synthesis of (3S, 5R, 3′S, 5′R)-Capsorubin

被引:3
作者
Frederico, Daniel [1 ]
Constantino, Mauricio G. [1 ]
Donate, Paulo M. [1 ]
机构
[1] Univ Sao Paulo, Dept Quim, Fac Filosofia Ciencias & Letras Ribeirao Preto, BR-14040901 Ribeirao Preto, SP, Brazil
基金
巴西圣保罗研究基金会;
关键词
carotenoid; capsorubin; crocetindial; cyclopentane keto-alkohol; synthesis; CAPSICUM-ANNUUM L; CAROTENOIDS; CAPSORUBIN; CAPSANTHIN; CANCER; REARRANGEMENT; LYCOPENE; ESTERS;
D O I
10.1590/S0103-50532009000500013
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The total synthesis of enantiomerically enriched (3S, 5R, 3' S, 5'R)-capsorubin (1) by aldol condensation of (1R, 4S)-1-(4-hydroxy-1,2,2-trimethyl-cyclopentyl)ethanone (2a) and crocetindial (3) is described. An alternative, short eight-step synthesis of the optically active compound 2a (ee 89%) is also reported.
引用
收藏
页码:888 / U148
页数:15
相关论文
共 50 条
[41]   Synthesis and crystal structures of the silylated lambda(5)-phosphazenes R-C(CH2PPh2NSiMe3)(3) with R = H and CH3 [J].
Schlecht, S ;
Faza, N ;
Massa, W ;
Weller, F ;
Dehnicke, K .
ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 1997, 623 (11) :1739-1743
[42]   The Synthesis of (2S, 3S, 4R)-2,3-Dialkyl-N-Phenyl-1,2,3,4-Tetrahydro-4-Quinolinamines in the Presence of Crystalline and Amorphous Aluminosilicates [J].
Grigor'eva, N. G. ;
Kostyleva, S. A. ;
Artem'eva, A. S. ;
Bubennov, S. V. ;
Kutepov, B. I. .
PETROLEUM CHEMISTRY, 2020, 60 (04) :525-531
[43]   Synthesis and Characterization of the R27S Genetic Variant of Insulin-like Peptide 5 [J].
Zaykov, Alexander N. ;
Gelfanov, Vasily M. ;
Liu, Fa ;
DiMarchi, Richard D. .
CHEMMEDCHEM, 2018, 13 (08) :852-859
[44]   Synthesis of lithium, sodium, cesium, and calcium salts of (E)-4- or (E,S)-3-methyl-2-(5-arylisoxazol-3-yl)-methyleneaminobutanoic, (E,S)-4-methyl-2- or (E,2S,3S)-3-methyl-2-(5-arylisoxazol-3-yl)methyleneaminopentanoic, and (E)-6-(5-arylisoxazol-3-yl)methyleneaminohexanoic acids [J].
E. A. Dikusar ;
V. I. Potkin ;
S. K. Pyatkevich .
Russian Journal of General Chemistry, 2014, 84 :1701-1705
[45]   Synthesis of lithium, sodium, cesium, and calcium salts of (E)-4-or (E,S)-3-methyl-2-(5-arylisoxazol-3-yl)-methyleneaminobutanoic, (E,S)-4-methyl-2-or (E,2S,3S)-3-methyl-2-(5-arylisoxazol-3-yl)methyleneaminopentanoic, and (E)-6-(5-arylisoxazol-3-yl)methyleneaminohexanoic acids [J].
Dikusar, E. A. ;
Potkin, V. I. ;
Pyatkevich, S. K. .
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2014, 84 (09) :1701-1705
[46]   (2R,3S)-Dihydroxybutanoic Acid Synthesis as a Novel Metabolic Function of Mutant Isocitrate Dehydrogenase 1 and 2 in Acute Myeloid Leukemia [J].
Idle, Jeffrey R. ;
Seipel, Katja ;
Bacher, Ulrike ;
Pabst, Thomas ;
Beyoglu, Diren .
CANCERS, 2020, 12 (10) :1-18
[47]   Synthesis of (S) and (R)-tilisolol hydrochloride [J].
Qian, Shan ;
Ye, Xiao Juan ;
Zheng, Fan ;
Yang, Li ;
Wu, Yong .
CHINESE CHEMICAL LETTERS, 2009, 20 (06) :648-650
[48]   Synthesis of(S) and(R)-tilisolol hydrochloride [J].
Shan QianXiao Juan YeFan ZhengLi YangYong Wu Key Laboratory of Drug TargetingWest China School of PharmacySichuan UniversityChengduSichuan China .
ChineseChemicalLetters, 2009, 20 (06) :648-650
[49]   Synthetic Study towards (+)-Clavosolide A: Synthesis of the Intermediate of (R)-methyl 5-hydroxy-3-oxoheptanoate [J].
Leng, Xiao ;
Xu, Tianxiang ;
Huang, Shuangping ;
Wang, Xiaoji .
PROCEEDINGS OF THE 2015 2ND INTERNATIONAL CONFERENCE ON MACHINERY, MATERIALS ENGINEERING, CHEMICAL ENGINEERING AND BIOTECHNOLOGY (MMECEB), 2016, 49 :820-823
[50]   Synthesis of (S, S)-1, 5-bis(4-alkyl-5-hydroxy-2-oxo-3-azapentyl)-1, 5-diazacyclooetane [J].
Shang, ZL ;
Shang, ZC ;
Yu, QS .
CHINESE CHEMICAL LETTERS, 2001, 12 (09) :769-770