Stereoselective total synthesis of enantiomerically pure 1-trifluoromethyl tetrahydroisoquinoline alkaloids

被引：0

作者：

Bravo, P ^{[1
]}

Crucianelli, M ^{[1
]}

Farina, A ^{[1
]}

Meille, SV ^{[1
]}

Volonterio, A ^{[1
]}

Zanda, M ^{[1
]}

机构：

[1] Politecn Milan, CNR, Ctr Studio Sostanze Organ Nat, Dipartimento Chim, I-20131 Milan, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 1998卷 / 03期

关键词：

beta-iminosulfoxides; quaternary stereocentre; Pictet-Spengler reaction; alkaloids; fluorine;

D O I：

10.1002/(SICI)1099-0690(199803)1998:3<435::AID-EJOC435>3.0.CO;2-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiomerically pure 1-trifluoromethyl-tetrahydroisoquinoline alkaloid analogues, in which C-1 is a quaternary stereogenic centre, have been synthesized by stereoselective intramolecular Pictet-Spengler reaction of the N-arylethyl gamma-trifluoro-beta-iminosulfoxide (R)-3, and subsequent elaborations of the sulfinyl auxiliary. The absolute stereochemistry of the stereogenic centre was determined by X-ray diffraction on the alpha-phenylpropionic ester (1R,2'S)-10.

引用

页码：435 / 440

页数：6

共 55 条

[1] TABLES OF BOND LENGTHS DETERMINED BY X-RAY AND NEUTRON-DIFFRACTION .1. BOND LENGTHS IN ORGANIC-COMPOUNDS [J].

ALLEN, FH ;

KENNARD, O ;

WATSON, DG ;

BRAMMER, L ;

ORPEN, AG ;

TAYLOR, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (12) :S1-S19

[2]

[Anonymous], 1991, Fluorine in Bioorganic Chemistry

[3] New versatile fluorinated chiral building blocks: Synthesis and reactivity of optically pure alpha-(fluoroalkyl)-beta-sulfinylenamines [J].

Arnone, A ;

Bravo, P ;

Capelli, S ;

Fronza, G ;

Meille, SV ;

Zanda, M ;

Cavicchio, G ;

Crucianelli, M .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10) :3375-3387

[4] New versatile fluorinated chiral building blocks: Synthesis and reactivity of optically pure alpha-(fluoroalkyl)-beta-sulfinylenamines (vol 61, pg 3383, 1996) [J].

Arnone, A ;

Bravo, P ;

Capelli, S ;

Fronza, G ;

Meille, SV ;

Zanda, M ;

Cavicchio, G ;

Crucianelli, M .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9635-9635

[5]

Banks R.E., 1994, ORGANOFLUORINE CHEM

[6] beta-Phenylethylamines and the isoquinoline alkaloids [J].

Bentley, KW .

NATURAL PRODUCT REPORTS, 1997, 14 (04) :387-411

[7] NEW METHOD FOR METHYLATION OF AMINES [J].

BORCH, RF ;

HASSID, AI .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (10) :1673-&

[8] CYANOHYDRIDOBORATE ANION AS A SELECTIVE REDUCING AGENT [J].

BORCH, RF ;

BERNSTEIN, MD ;

DURST, HD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (12) :2897-+

[9]

Bravo P, 1996, SYNLETT, P887

[10]

BURGER K, 1989, CHEM ZTG, V113, P277

← 1 2 3 4 5 6 →