Synthetic studies on ecteinascidin 743: rapid access to the fully functionalized tetrahydroisoquinoline with a bridged 10-membered sulfur containing macrocycle

被引:30
作者
De Paolis, M [1 ]
Chiaroni, A [1 ]
Zhu, JP [1 ]
机构
[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
关键词
D O I
10.1039/b309824a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Synthesis of tetrahydroisoquinoline with a 1,4- bridged 10- membered sulfur containing macrolactone ( 5) is described. Phenolic aldolisation, Pictet - Spengler cyclisation of an acid sensitive amino diol under newly developed conditions ( LiBr, toluene - TFE, 80 degrees C) and acid promoted intramolecular C - S bond formation leading to a 10- membered cycle are key steps of our synthesis.
引用
收藏
页码:2896 / 2897
页数:2
相关论文
共 29 条
[1]  
Arai T., 1983, ALKALOIDS, V21, P55
[2]   SYNTHESIS OF 1-(2-HYDROXYARYL)-1,2,3-PROPANETRIOL AND 1-(2-HYDROXYARYL)-2-AMINO-1,3-PROPANEDIOL DERIVATIVES OF EITHER THREO OR ERYTHRO CONFIGURATION [J].
CASIRAGHI, G ;
CORNIA, M ;
RASSU, G .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (21) :4919-4922
[3]   Enantioselective total synthesis of ecteinascidin 743 [J].
Corey, EJ ;
Gin, DY ;
Kania, RS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (38) :9202-9203
[4]   THE PICTET-SPENGLER CONDENSATION - A NEW DIRECTION FOR AN OLD REACTION [J].
COX, ED ;
COOK, JM .
CHEMICAL REVIEWS, 1995, 95 (06) :1797-1842
[5]   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
[6]   N-carbamate-assisted stereoselective synthesis of chiral vicinal amino sulfides [J].
De Paolis, M ;
Blankenstein, J ;
Bois-Choussy, M ;
Zhu, JP .
ORGANIC LETTERS, 2002, 4 (07) :1235-1238
[7]   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
[8]  
Endo A, 1999, SYNLETT, P1103
[9]   Sequential Staudinger/Pictet-Spengler cyclization strategy for the construction of tetrahydroisoquinolines of the bioxalomycin and ecteinascidin family of alkaloids [J].
Herberich, B ;
Kinugawa, M ;
Vazquez, A ;
Williams, RM .
TETRAHEDRON LETTERS, 2001, 42 (04) :543-546
[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