Diastereoselective synthesis of functionalised carbazoles via a sequential Diels-Alder/ene reaction strategy

被引：26

作者：

Cowell, Joseph ^{[1
]}

Abualnaja, Matokah ^{[1
]}

Morton, Stephanie ^{[1
]}

Linder, Ruth ^{[1
]}

Buckingham, Faye ^{[1
]}

Waddell, Paul G. ^{[1
]}

Probert, Michael R. ^{[1
]}

Hall, Michael J. ^{[1
]}

机构：

[1] Newcastle Univ, Sch Chem, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England

来源：

RSC ADVANCES | 2015年 / 5卷 / 21期

基金：

英国工程与自然科学研究理事会;

关键词：

VITRO ANTIPROLIFERATIVE ACTIVITIES; ENE REACTION; DOMINO REACTIONS; 3-VINYLINDOLES; CARBODIENOPHILES; 2-VINYLINDOLES; STAUROSPORINE; VINYLINDENES; ALKALOIDS; ANALOGS;

D O I：

10.1039/c5ra00499c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An operationally simple one-pot, three-component, diastereoselective synthesis of saturated carbazoles and related pyridazino[3,4-b] indoles, based on two sequential intermolecular pericyclic reactions, is described. The reaction sequence involves an intermolecular Diels-Alder (D-A) reaction of a 3-vinyl-1H-indole, containing an electron withdrawing N-protecting group, with a suitable dienophile. Due to the electron withdrawing nature of the N-protecting group the resultant D-A cycloadducts are sufficiently stabilised to allow for a subsequent in situ diastereospecific intermolecular ene reaction to take place with an added enophile, generating functionalised carbazoles with relative stereocontrol of up to four stereocentres.

引用

页码：16125 / 16152

页数：28

共 50 条

[41] Synthesis of a new versatile dienophile and its use in a highly diastereoselective Diels-Alder reaction
Renaud, JL
Aubert, C
Malacria, M
TETRAHEDRON LETTERS, 1999, 40 (27) : 5015 - 5018
[42] Chiral shift reagent catalyzed, diastereoselective imino Diels-Alder reaction - Synthesis of pyrazolyltetrahydroquinolines
Sridhar, R
Perumal, PT
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2006, 84 (03): : 464 - 468
[43] DIASTEREOSELECTIVE DIELS-ALDER REACTIONS VIA CYCLIC VINYLOXOCARBENIUM IONS
SAMMAKIA, T
BERLINER, MA
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21): : 6652 - 6653
[44] A formal asymmetric synthesis of (-)-epibatidine using a highly diastereoselective hetero Diels-Alder reaction
Cabanal-Duvillard, I
Berrien, JF
Ghosez, L
Husson, HP
Royer, J
TETRAHEDRON, 2000, 56 (23) : 3763 - 3769
[45] Synthesis of highly substituted cyclohexenes via traceless Diels-Alder and sulfinyl retro-ene tandem reaction
Choi, Jin
Park, Hoyoon
Yoo, Hyun Jung
Lee, Chulbom
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 246
[46] Highly diastereoselective synthesis of novel polymers via tandem Diels-Alder-ene reactions
Mallakpour, SE
Hajipour, AR
Mahdavian, AR
Rafiemanzelat, F
POLYMER INTERNATIONAL, 1999, 48 (02) : 109 - 116
[47] A DIRECT TOTAL SYNTHESIS OF (+)-LONGIFOLENE VIA AN INTRAMOLECULAR DIELS-ALDER STRATEGY
LEI, B
FALLIS, AG
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) : 4609 - 4610
[48] Synthesis of polycyclic oxanorbornanes via a sequential epoxyhexopyranoside ring contraction-intramolecular Diels-Alder reaction
Ponten, F
Magnusson, G
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (23): : 7978 - 7983
[49] SYNTHESIS OF NITROSUBSTITUTED DECALONES BY DOUBLE MICHAEL REACTION, SEQUENTIAL MICHAEL REACTION, AND BY DIELS-ALDER REACTION
RICHTER, F
OTTO, HH
TETRAHEDRON LETTERS, 1987, 28 (26) : 2945 - 2946
[50] Total synthesis of endiandric acid A via an intramolecular Diels-Alder strategy
May, SA
Grieco, PA
Lee, HH
SYNLETT, 1997, (05) : 493 - &

← 1 2 3 4 5 →