A convergent synthesis of the macrocyclic core of cytotrienins: Application of RCM for macrocyclization

被引:72
作者
Evano, G
Schaus, JV
Panek, JS
机构
[1] Boston Univ, Dept Chem, Boston, MA 02215 USA
[2] Boston Univ, Ctr Chem Methodol & Library Dev, Boston, MA 02215 USA
关键词
D O I
10.1021/ol036284k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The asymmetric synthesis of the fully elaborated macrocyclic core of cytotrienins A-D, potent apoptosis-inducing agents, is described. Synthetic highlights include the construction of the aniline bond using a copper-mediated amidation and the use of a ring-closing metathesis (RCM) reaction to efficiently install the (E,E,E)-triene and simultaneously construct the macrocyclic lactam.
引用
收藏
页码:525 / 528
页数:4
相关论文
共 29 条
[1]   The anti-selective boron-mediated asymmetric aldol reaction of carboxylic esters [J].
Abiko, A ;
Liu, JF ;
Masamune, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (10) :2586-2587
[2]   C-13 NMR CHEMICAL-SHIFT CORRELATIONS IN 1,3-DIOL ACETONIDES - IMPLICATIONS FOR THE STEREOCHEMICAL ASSIGNMENT OF PROPIONATE-DERIVED POLYOLS [J].
EVANS, DA ;
RIEGER, DL ;
GAGE, JR .
TETRAHEDRON LETTERS, 1990, 31 (49) :7099-7100
[3]  
FUNYAMA S, 1985, J ANTIBIOT, V38, P1107
[4]  
FUNYAMA S, 1985, J ANTIBIOT, V38, P1677
[5]  
Fürstner A, 2000, ANGEW CHEM INT EDIT, V39, P3012
[6]   THIAZINOTRIENOMYCINS, NEW ANSAMYCIN GROUP ANTIBIOTICS [J].
HOSOKAWA, N ;
NAGANAWA, H ;
IINUMA, H ;
HAMADA, M ;
TAKEUCHI, T ;
KANBE, T ;
HORI, M .
JOURNAL OF ANTIBIOTICS, 1995, 48 (06) :471-478
[7]   DIBAL-H-H2NR and DIBAL-H-HNR1R2•HCl complexes for efficient conversion of lactones and esters to amides [J].
Huang, PQ ;
Zheng, X ;
Deng, XM .
TETRAHEDRON LETTERS, 2001, 42 (51) :9039-9041
[8]   Boron-mediated aldol reaction of carboxylic esters: Complementary anti- and syn-selective asymmetric aldol reactions [J].
Inoue, T ;
Liu, JF ;
Buske, DC ;
Abiko, A .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (15) :5250-5256
[9]   Cytotrienin A, a novel apoptosis inducer in human leukemia HL-60 cells [J].
Kakeya, H ;
Zhang, HP ;
Kobinata, K ;
Onose, R ;
Onozawa, C ;
Kudo, T ;
Osada, H .
JOURNAL OF ANTIBIOTICS, 1997, 50 (04) :370-372
[10]   AN ACYLNITROSO CYCLOADDITION APPROACH TO THE SYNTHESIS OF HIGHLY OXYGENATED INDOLIZIDINE ALKALOIDS [J].
KECK, GE ;
ROMER, DR .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (22) :6083-6089