Synthesis of (-)-amphidinolide K fragment C9-C22

被引:50
作者
Andreou, T [1 ]
Costa, AM [1 ]
Esteban, L [1 ]
Gonzàlez, L [1 ]
Mas, G [1 ]
Vilarrasa, J [1 ]
机构
[1] Univ Barcelona, Dept Quim Organ, E-08028 Barcelona, Catalonia, Spain
关键词
D O I
10.1021/ol051200o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The key fragment (2a or 2b) in a total synthesis of the cytotoxic macrolide (-)-amphidinolide K (1) has been achieved from synthons U-CA (3) and C15-C22 (4), which have both been prepared from glutamic acid in good overall yields.
引用
收藏
页码:4083 / 4086
页数:4
相关论文
共 33 条
[1]  
CAGE JR, 1989, ORG SYNTH, V68, P77
[2]   SYNTHESIS OF BOTH THE ENANTIOMERS OF 4-DODECANOLIDE, THE PHEROMONE OF THE ROVE BEETLE [J].
CHATTOPADHYAY, S ;
MAMDAPUR, VR ;
CHADHA, MS .
TETRAHEDRON, 1990, 46 (10) :3667-3672
[3]   Asymmetric aldol additions:: Use of titanium tetrachloride and (-)-sparteine for the soft enolization of N-acyl oxazolidinones, oxazolidinethiones, and thiazolidinethiones [J].
Crimmins, MT ;
King, BW ;
Tabet, EA ;
Chaudhary, K .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (03) :894-902
[4]   Asymmetric aldol additions with titanium enolates of acyloxazolidinethiones: Dependence of selectivity on amine base and Lewis acid stoichiometry [J].
Crimmins, MT ;
King, BW ;
Tabet, EA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (33) :7883-7884
[5]   REACTIVITY OF BETA-AMINO ALCOHOLS WITH CARBON-DISULFIDE - STUDY ON THE SYNTHESIS OF 2-OXAZOLIDINETHIONES AND 2-THIAZOLIDINETHIONES [J].
DELAUNAY, D ;
TOUPET, L ;
LECORRE, M .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (20) :6604-6607
[6]   READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156
[7]   From (E)- and (Z)-ketoximes to N-sulfenylimines, ketimines or ketones at will.: Application to erythromycin derivatives [J].
Esteban, J ;
Costa, AM ;
Urpí, F ;
Vilarrasa, J .
TETRAHEDRON LETTERS, 2004, 45 (29) :5563-5567
[8]   NEW PROCEDURE FOR THE DIRECT GENERATION OF TITANIUM ENOLATES - DIASTEREOSELECTIVE BOND CONSTRUCTIONS WITH REPRESENTATIVE ELECTROPHILES [J].
EVANS, DA ;
URPI, F ;
SOMERS, TC ;
CLARK, JS ;
BILODEAU, MT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) :8215-8216
[9]  
Evans DA, 2003, ACTUAL CHIMIQUE, P35
[10]   TOTAL SYNTHESIS OF (+)-CALYCULIN-A [J].
EVANS, DA ;
GAGE, JR ;
LEIGHTON, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (24) :9434-9453