Synthetic approaches towards alkaloids bearing α-tertiary amines

被引:174
作者
Hager, Anastasia
Vrielink, Nina
Hager, Dominik
Lefranc, Julien
Trauner, Dirk [1 ]
机构
[1] Univ Munich, Fak Chem & Pharm, Butenandtstr 5-13, D-81377 Munich, Germany
关键词
ENANTIOSELECTIVE TOTAL-SYNTHESIS; EFFICIENT TOTAL-SYNTHESIS; CONCISE TOTAL-SYNTHESIS; FORMAL TOTAL-SYNTHESIS; BIOMIMETIC TOTAL-SYNTHESIS; ASYMMETRIC TOTAL-SYNTHESIS; (-)-N-METHYLWELWITINDOLINONE C ISOTHIOCYANATE; NICOTINIC ACETYLCHOLINE-RECEPTOR; BIOACTIVE NATURAL-PRODUCTS; AZA-PRINS CYCLIZATION;
D O I
10.1039/c5np00096c
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Alkaloids account for some of the most beautiful and biologically active natural products. Although they are usually classified along biosynthetic criteria, they can also be categorized according to certain structural motifs. Amongst these, the alpha-tertiary amine (ATA), i.e. a tetrasubstituted carbon atom surrounded by three carbons and one nitrogen, is particularly interesting. A limited number of methods have been described to access this functional group and fewer still are commonly used in synthesis. Herein, we review some approaches to asymmetrically access ATAs and provide an overview of alkaloid total syntheses where those have been employed.
引用
收藏
页码:491 / 522
页数:32
相关论文
共 404 条
[1]   Natural products from Cephalotaxus sp.: chemical diversity and synthetic aspects [J].
Abdelkafi, Hajer ;
Nay, Bastien .
NATURAL PRODUCT REPORTS, 2012, 29 (08) :845-869
[2]   Total synthesis of the tricyclic marine alkaloids (-)-lepadiformine, (+)-cylindricine C, and (-)-fasicularin via a common intermediate formed by formic acid-induced intramolecular conjugate azaspirocyclization [J].
Abe, H ;
Aoyagi, S ;
Kibayashi, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (05) :1473-1480
[3]   Synthetic approaches towards huperzine A and B [J].
Abu Sohel, Shariar Md ;
Opatz, Till .
ARKIVOC, 2014, :92-108
[4]   10,22-DIOXOKOPSANE NA-METHYL-10,22-DIOXOKOPSANE AND NA-CARBOMETHOXY-10,22-DIOXOKOPSANE . 3 NEW ALKALOIDS OF PLEIOCARPA MUTICA BENTH [J].
ACHENBACH, H ;
BIEMANN, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (21) :4944-+
[5]   Total Synthesis of (-)-Histrionicotoxin (vol 13, pg 4466, 2011) [J].
Adachi, Yohei ;
Kamei, Noriyuki ;
Yokoshima, Satoshi ;
Fukuyama, Tohru .
ORGANIC LETTERS, 2014, 16 (04) :1273-1273
[6]   Total Synthesis of (-)-Histrionicotoxin [J].
Adachi, Yohei ;
Kamei, Noriyuki ;
Yokoshima, Satoshi ;
Fukuyama, Tohru .
ORGANIC LETTERS, 2011, 13 (16) :4446-4449
[7]  
ALBUQUERQUE EX, 1974, J PHARMACOL EXP THER, V189, P513
[8]  
ALDER K, 1956, LIEBIGS ANN CHEM, V601, P138
[9]  
ALDER K, 1953, CHEM BER-RECL, V86, P1544
[10]  
ALDER K, 1959, LIEBIGS ANN CHEM, V620, P73