Recent applications of imines as key intermediates in the synthesis of alkaloids and novel nitrogen heterocycles

被引：137

作者：

Martin, Stephen F. ^{[1
]}

机构：

[1] Univ Texas Austin, Dept Chem & Biochem, Austin, TX 78712 USA

来源：

PURE AND APPLIED CHEMISTRY | 2009年 / 81卷 / 02期

关键词：

imines; Mannich reaction; multicomponent reactions; cascade reactions; alkaloid synthesis; diversity-oriented synthesis; VINYLOGOUS MANNICH REACTIONS; N-ACYLIMINIUM IONS; RING-CLOSING METATHESIS; ENANTIOSELECTIVE SYNTHESIS; MULTICOMPONENT REACTIONS; QUINOLIZIDINE ALKALOIDS; ASYMMETRIC-SYNTHESIS; (+/-)-PINNAIC ACID; DIASTEREOSELECTIVE REDUCTION; CONCISE SYNTHESES;

D O I：

10.1351/PAC-CON-08-07-03

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

One of the major challenges in contemporary synthetic organic chemistry is the design and development of new tactics and strategies and their application to concise and efficient syntheses of biologically active natural products. Strategies that utilize reactions that enable the rapid assembly of the skeletal framework of such targets are thus especially attractive. In this context, we have developed novel applications of imine chemistry in Mannich and related reactions, cascade processes, and multicomponent reactions (MCRs) to rapidly assemble structural subunits common to diverse families of alkaloids. The practical utility of these chemistries is evidenced by their use in the execution of facile total syntheses of (+/-)-epilupinine (1), (+/-)-tashiromine (2), (-)-epimyrtine (3), and (+/-)-roelactamine (4) as well as other nitrogen heterocycles of potential biological interest.

引用

页码：195 / 204

页数：10

共 55 条

[1] Cascade iminium ion reactions for the facile synthesis of quinolizidines.: Concise syntheses of (±)-epilupinine and (-)-epimyrtine [J].

Amorde, SM ;

Judd, AS ;

Martin, SF .

ORGANIC LETTERS, 2005, 7 (10) :2031-2033

[2] Formal syntheses of (+/-)-pinnaic acid and (+/-)-halichlorine [J].

Andrade, RB ;

Martin, SF .

ORGANIC LETTERS, 2005, 7 (25) :5733-5735

[3] The pyridinium reduction route to alkaloids:: a synthesis of (±)-tashiromine [J].

Bates, RW ;

Boonsombat, J .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (07) :654-656

[4] VINYLSILANE-TERMINATED AND ALKYNYLSILANE-TERMINATED CYCLIZATION REACTIONS [J].

BLUMENKOPF, TA ;

OVERMAN, LE .

CHEMICAL REVIEWS, 1986, 86 (05) :857-873

[5] Determination of the nucleophilicities of silyl and alkyl enol ethers [J].

Burfeindt, J ;

Patz, M ;

Müller, M ;

Mayr, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (15) :3629-3634

[6] A planning strategy for diversity-oriented synthesis [J].

Burke, MD ;

Schreiber, SL .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (01) :46-58

[7] A simple and efficient synthetic route to chiral isopavines. Synthesis of (-)-O-methylthalisopavine and (-)-amurensinine [J].

Carrillo, L ;

Badia, D ;

Dominguez, E ;

Vicario, JL ;

Tellitu, I .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (20) :6716-6721

[8] Total synthesis of (±)-halichlorine, (±)-pinnaic acid, and (±)-tauropinnaic acid [J].

Christie, HS ;

Heathcock, CH .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (33) :12079-12084

[9] ADDITION OF METALLO ENOLATES TO 1-ACYLPYRIDINIUM SALTS - A SHORT SYNTHESIS OF (+/-)-EPI-LUPININE [J].

COMINS, DL ;

BROWN, JD .

TETRAHEDRON LETTERS, 1986, 27 (20) :2219-2222

[10] Asymmetric synthesis of the quinolizidine alkaloid (-)-epimyrtine with intramolecular Mannich Cyclization and n-sulfinyl δ-amino β-ketoesters [J].

Davis, FA ;

Mang, Y ;

Anilkumar, G .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (21) :8061-8064

← 1 2 3 4 5 6 →