Recent Advances in the Total Synthesis of Clavaminols

被引:1
作者
Jin, Tian [1 ]
Zhao, Lu [2 ]
Liu, Xiao [1 ]
Sun, Liang [3 ]
Lin, Jia-Fu [1 ]
Zheng, Zhe-Bin [1 ]
机构
[1] Chengdu Univ, Sichuan Ind Inst Antibiot, Sichuan Educ Dept, Key Lab Med & Edible Plants Resources Dev, Chengdu 610052, Sichuan, Peoples R China
[2] Sichuan Inst Food & Drug Control, Chengdu 611731, Sichuan, Peoples R China
[3] Jilin Prov Peoples Hosp, Dept Pharm, Changchun 130021, Jilin, Peoples R China
来源
SYNTHESIS-STUTTGART | 2018年 / 50卷 / 23期
关键词
total synthesis; clavaminols; natural products; long-chain; 2-amino-3-alkanols; antitumor activity; STEREOSELECTIVE TOTAL-SYNTHESIS; METATHESIS REACTIONS; SECONDARY ALCOHOLS; PRACTICAL ROUTE; OXIDATION; (-)-CLAVAMINOL; SPHINGANINE; DERIVATIVES; AMINATION; CHLORIDE;
D O I
10.1055/s-0037-1610305
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Clavaminols are a new class of long-chain 2-amino-3-lkanols that mostly contain 2R, 3S-configurations. Owing to their interesting molecular architectures and promising activities, they have become popular targets for synthetic organic chemists. In this review, we highlight 12 total syntheses of clavaminols from different research groups during the period 2009 to 2018.
引用
收藏
页码:4569 / 4576
页数:8
相关论文
共 55 条
[1]   Clavaminols A-F, novel cytotoxic 2-amino-3-alkanols from the ascidian Clavelina phlegraea [J].
Aiello, Anna ;
Fattorusso, Ernesto ;
Giordano, Antonella ;
Menna, Marialuisa ;
Navarrete, Carmen ;
Munoz, Eduardo .
BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (08) :2920-2926
[2]   Clavaminols G-N, six new marine sphingoids from the Mediterranean ascidian Clavelina phlegraea [J].
Aiello, Anna ;
Fattorusso, Ernesto ;
Giordano, Antonella ;
Menna, Marialuisa ;
Navarrete, Carmen ;
Munoz, Eduardo .
TETRAHEDRON, 2009, 65 (22) :4384-4388
[3]   Asymmetric Synthesis of Sphinganine and Clavaminol H [J].
Ait-Youcef, Ramzi ;
Moreau, Xavier ;
Greck, Christine .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (15) :5312-5315
[4]   Asymmetric α-Amination of Chiral Protected β-Hydroxyaldehydes Catalyzed by Proline [J].
Ait-Youcef, Ramzi ;
Sbargoud, Kamal ;
Moreau, Xavier ;
Greck, Christine .
SYNLETT, 2009, (18) :3007-3010
[5]   ASYMMETRIC REARRANGEMENT OF ALLYLIC TRICHLOROACETIMIDATES: PREPARATION OF (S)-2,2,2-TRICHLORO-N-(1-PROPYLALLYL) ACETAMIDE (Acetamide, 2,2,2-trichloro-N-[(1S)-1-ethenylbutyl]-) [J].
Anderson, Carolyn E. ;
Overman, Larry E. ;
Watson, Mary P. .
ORGANIC SYNTHESES, 2005, 82 :134-+
[6]   Cross-metathesis assisted by microwave irradiation [J].
Bargiggia, FC ;
Murray, WV .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (23) :9636-9639
[7]   Asymmetric organocatalytic β-hydroxylation of α,β-unsaturated aldehydes [J].
Bertelsen, Soren ;
Diner, Peter ;
Johansen, Rasmus Lyng ;
Jorgensen, Karl Anker .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (06) :1536-+
[8]   HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS [J].
BLANCHETTE, MA ;
CHOY, W ;
DAVIS, JT ;
ESSENFELD, AP ;
MASAMUNE, S ;
ROUSH, WR ;
SAKAI, T .
TETRAHEDRON LETTERS, 1984, 25 (21) :2183-2186
[9]   THE USE OF 2-DEOXY-2-TRICHLOROACETAMIDO-D-GLUCOPYRANOSE DERIVATIVES IN SYNTHESES OF OLIGOSACCHARIDES [J].
BLATTER, G ;
BEAU, JM ;
JACQUINET, JC .
CARBOHYDRATE RESEARCH, 1994, 260 (02) :189-202
[10]   Diastereoselective synthesis and bioactivity of long-chain anti-2-amino-3-alkanols [J].
Chen, Bi-Shuang ;
Yang, Long-He ;
Ye, Jian-Liang ;
Huang, Tao ;
Ruan, Yuan-Ping ;
Fu, Jin ;
Huang, Pei-Qiang .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (11) :5480-5486