Studies on the Claisen rearrangements in the indolo[2,3-b]quinoline system

被引：20

作者：

Voute, Nicholas ^{[1
]}

Philp, Douglas ^{[1
]}

Slawin, Alexandra M. Z. ^{[1
]}

Westwood, Nicholas J. ^{[1
]}

机构：

[1] Univ St Andrews, Sch Chem & Biomed Sci Res Complex, St Andrews KY16 9ST, Fife, Scotland

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2010年 / 8卷 / 02期

基金：

英国工程与自然科学研究理事会;

关键词：

ENANTIOSELECTIVE TOTAL-SYNTHESIS; TRANSITION-STATE STRUCTURE; QUATERNARY CARBON CENTERS; SYNTHETIC APPROACH; CALYCANTHACEOUS ALKALOIDS; PENICILLIUM-EXPANSUM; BIOMIMETIC APPROACH; TANDEM OLEFINATION; ORGANIC-SYNTHESIS; RING-SYSTEM;

D O I：

10.1039/b915677a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A study of the effect of substrate structure on a Claisen-aza-Cope reaction is presented including a rationalisation of the reaction outcome using DFT calculations. An asymmetric version of the reaction is also described that is of relevance to a proposed approach to the communesin family of natural products.

引用

页码：442 / 450

页数：9

共 52 条

[1] Penicillium expansum:: Consistent production of patulin, chaetoglobosins, and other secondary metabolites in culture and their natural occurrence in fruit products [J].

Andersen, B ;

Smedsgaard, J ;

Frisvad, JC .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2004, 52 (08) :2421-2428

[2] LARGER SCALE PREPARATION OF OPTICALLY-ACTIVE ALLYLIC ALCOHOLS [J].

BALMER, E ;

GERMAIN, A ;

JACKSON, WP ;

LYGO, B .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (04) :399-400

[3] Studies of the reactions between indole-2,3-diones (isatins) and 2-aminobenzylamine [J].

Bergman, J ;

Engqvist, R ;

Stålhandske, C ;

Wallberg, H .

TETRAHEDRON, 2003, 59 (07) :1033-1048

[4] REDUCTION AND STEREOCHEMICAL STUDIES THROUGH NMR AND X-RAY TECHNIQUES OF INDOLO[2,1-B]QUINAZOLINES [J].

BERGMAN, J ;

TILSTAM, U ;

TORNROOS, KW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (03) :519-527

[5] A new Claisen sequence for the synthesis of 3-substituted-2-oxindoles [J].

Booker-Milburn, KI ;

Fedouloff, M ;

Paknoham, SJ ;

Strachan, JB ;

Melville, JL ;

Voyle, M .

TETRAHEDRON LETTERS, 2000, 41 (23) :4657-4661

[6] Claisen rearrangement over the past nine decades [J].

Castro, AMM .

CHEMICAL REVIEWS, 2004, 104 (06) :2939-3002

[7] Stereoselective construction of quaternary stereocenters [J].

Christoffers, J ;

Baro, A .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) :1473-1482

[8]

Christoffers J, 2001, ANGEW CHEM INT EDIT, V40, P4591, DOI 10.1002/1521-3773(20011217)40:24<4591::AID-ANIE4591>3.0.CO

[9]

2-V

[10] THE CHEMISTRY OF 2H-1,3-BENZOXAZINE-2,4-(1H)DIONE (ISATOIC ANHYDRIDE) .8. A ONE-STEP SYNTHESIS OF THE QUININDOLINE RING-SYSTEM AND RELATED-COMPOUNDS [J].

COPPOLA, GM .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1980, 17 (08) :1785-1787

← 1 2 3 4 5 6 →