Synthesis of enantiopure (2R,3aS,7aS)-2-ethyloctahydroindol-6-one and its Fischer indolization

被引：16
作者：
Bonjoch, J
Catena, J
Terricabras, D
Fernandez, JC
LopezCanet, M
Valls, N
机构：
[1] Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona
来源：
TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 18期
关键词：
D O I：
10.1016/S0957-4166(97)00379-0
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
A diastereoselective synthesis of (-)-2-ethyloctahydroindol-6-one 12 starting from O-methyl-L-tyrosine 1 is described. The process first involves the synthesis of enantiopure (-)-1-(4-methoxyphenyl)-2-butylamine 8, which, after Birch reduction, N-benzylation and acid treatment, renders the cis-fused azabicyclo 12. Studies on the Fischer indolization of 12 are also reported. (C) 1997 Elsevier Science Ltd.
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页码：3143 / 3151
页数：9
相关论文
共 27 条
[21]  
RABIDEAU PW, 1992, Z ORG REACT, V42, P1
[22]   NONRACEMIZING SYNTHESIS AND STEREOSELECTIVE REDUCTION OF CHIRAL ALPHA-AMINO KETONES [J].
REETZ, MT ;
DREWES, MW ;
LENNICK, K ;
SCHMITZ, A ;
HOLDGRUN, X .
TETRAHEDRON-ASYMMETRY, 1990, 1 (06) :375-378
[23]   PROTECTIVE GROUP TUNING IN THE STEREOSELECTIVE CONVERSION OF ALPHA-AMINO ALDEHYDES INTO AMINOALKYL EPOXIDES [J].
REETZ, MT ;
BINDER, J .
TETRAHEDRON LETTERS, 1989, 30 (40) :5425-5428
[24]   NEW APPROACHES TO THE USE OF AMINO-ACIDS AS CHIRAL BUILDING-BLOCKS IN ORGANIC-SYNTHESIS [J].
REETZ, MT .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (12) :1531-1546
[25]  
SAXTON JE, 1994, CHEM HETEROCYCLIC CO, V25, P487
[26]   SYNTHESE EINES VASPORESSORISCH WIRKENDEN PEPTIDS - [0-METHYL-TYROSIN]2-LYSIN8-VASOPRESSIN (OMTLV) [J].
SIEDEL, W ;
STURM, K ;
GEIGER, R .
CHEMISCHE BERICHTE-RECUEIL, 1963, 96 (05) :1436-&
[27]   DETERMINATION OF ENANTIOMERIC PURITY OF TERTIARY-AMINES BY H-1-NMR OF ALPHA-METHOXY-ALPHA-(TRIFLUOROMETHYL)PHENYLACETIC ACID COMPLEXES [J].
VILLANI, FJ ;
COSTANZO, MJ ;
INNERS, RR ;
MUTTER, MS ;
MCCLURE, DE .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (19) :3715-3718
123