A short enantioselective synthesis of protected L-3-hydroxy-4-methoxy-5-methyl phenylalanine and its corresponding aldehyde - A common subunit of ecteinascidin-743, safracin and congeners

被引:21
作者
De Paolis, M [1 ]
Chen, XC [1 ]
Zhu, JP [1 ]
机构
[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
关键词
amino acid; Ecteinascidin; 743; phase transfer catalyst; glycine template; L-DOPA derivative;
D O I
10.1055/s-2004-817763
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An asymmetric synthesis of appropriately protected L-3-hydroxy-4-methoxy-5-methyl phenylalanine from 3-methyl-catechol is described featuring a key enantioselective alkylation step.
引用
收藏
页码:729 / 731
页数:3
相关论文
共 25 条
[1]   A convergent enantioselective synthesis of the tetrahydroisoquinoline unit in the spiro ring of ecteinascidin 743 [J].
Corey, EJ ;
Gin, DY .
TETRAHEDRON LETTERS, 1996, 37 (40) :7163-7166
[2]   Enantioselective total synthesis of ecteinascidin 743 [J].
Corey, EJ ;
Gin, DY ;
Kania, RS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (38) :9202-9203
[3]   A rational approach to catalytic enantioselective enolate alkylation using a structurally rigidified and defined chiral quaternary ammonium salt under phase transfer conditions [J].
Corey, EJ ;
Xu, F ;
Noe, MC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) :12414-12415
[4]   Synthesis of ecteinascidin ET-743 and phthalascidin Pt-650 from cyanosafracin B [J].
Cuevas, C ;
Pérez, M ;
Martín, MJ ;
Chicharro, JL ;
Fernández-Rivas, C ;
Flores, M ;
Francesch, A ;
Gallego, P ;
Zarzuelo, M ;
de la Calle, F ;
García, J ;
Polanco, C ;
Rodríguez, I ;
Manzanares, I .
ORGANIC LETTERS, 2000, 2 (16) :2545-2548
[5]   Synthetic studies on ecteinascidin 743: rapid access to the fully functionalized tetrahydroisoquinoline with a bridged 10-membered sulfur containing macrocycle [J].
De Paolis, M ;
Chiaroni, A ;
Zhu, JP .
CHEMICAL COMMUNICATIONS, 2003, (23) :2896-2897
[6]   Total synthesis of ecteinascidin 743 [J].
Endo, A ;
Yanagisawa, A ;
Abe, M ;
Tohma, S ;
Kan, T ;
Fukuyama, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (23) :6552-6554
[7]  
Endo A, 1999, SYNLETT, P1103
[8]  
HELMCHEN G, 1972, TETRAHEDRON LETT, P3873
[9]   SAFRACINS, NEW ANTI-TUMOR ANTIBIOTICS .3. BIOLOGICAL-ACTIVITY [J].
IKEDA, Y ;
SHIMADA, Y ;
HONJO, K ;
OKUMOTO, T ;
MUNAKATA, T .
JOURNAL OF ANTIBIOTICS, 1983, 36 (10) :1290-1294
[10]   Synthetic studies on ecteinascidin-743: Constructing a versatile pentacyclic intermediate for the synthesis of ecteinascidins and saframycins [J].
Jin, W ;
Metobo, S ;
Williams, RM .
ORGANIC LETTERS, 2003, 5 (12) :2095-2098