Cascade polycyclizations in natural product synthesis

被引：227

作者：

Ardkhean, R. ^{[1
]}

Caputo, D. F. J. ^{[1
]}

Morrow, S. M. ^{[1
]}

Shi, H. ^{[1
]}

Xiong, Y. ^{[1
]}

Anderson, E. A. ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, 12 Mansfield Rd, Oxford OX1 3TA, England

来源：

CHEMICAL SOCIETY REVIEWS | 2016年 / 45卷 / 06期

基金：

英国工程与自然科学研究理事会;

关键词：

EPOXIDE-OPENING CASCADES; COLLECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; NICHOLAS REACTION; DRUG DISCOVERY; GOLD CATALYSIS; ALKALOIDS; CYCLIZATION; CORE; CYCLOISOMERIZATION;

D O I：

10.1039/c5cs00105f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Cascade (domino) reactions have an unparalleled ability to generate molecular complexity from relatively simple starting materials; these transformations are particularly appealing when multiple rings are forged during this process. In this tutorial review, we cover recent highlights in cascade polycyclizations as applied to natural product synthesis, including pericyclic, heteroatom-mediated, cationic, metal-catalyzed, organocatalytic, and radical sequences.

引用

页码：1557 / 1569

页数：13

共 55 条

[1] Cascade polycyclisations in natural product synthesis [J].

Anderson, Edward A. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (11) :3997-4006

[2] Biogenetically Inspired Total Syntheses of Lycopodium Alkaloids, (+)-Flabellidine and (-)-Lycodine [J].

Azuma, Masayuki ;

Yoshikawa, Tetsuya ;

Kogure, Noriyuki ;

Kitajima, Mariko ;

Takayama, Hiromitsu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (33) :11618-11621

[3] Industrial natural product chemistry for drug discovery and development [J].

Bauer, Armin ;

Broenstrupt, Mark .

NATURAL PRODUCT REPORTS, 2014, 31 (01) :35-60

[4] Biosynthetic and biomimetic electrocyclizations [J].

Beaudry, CM ;

Malerich, JP ;

Trauner, D .

CHEMICAL REVIEWS, 2005, 105 (12) :4757-4778

[5] Total Synthesis of Incarviditone and Incarvilleatone [J].

Brown, Patrick D. ;

Willis, Anthony C. ;

Sherburn, Michael S. ;

Lawrence, Andrew L. .

ORGANIC LETTERS, 2012, 14 (17) :4537-4539

[6] Natural product and natural product derived drugs in clinical trials [J].

Butler, Mark S. ;

Robertson, Avril A. B. ;

Cooper, Matthew A. .

NATURAL PRODUCT REPORTS, 2014, 31 (11) :1612-1661

[7] Gold(I) as an Artificial Cyclase: Short Stereodivergent Syntheses of (-)-Epiglobulol and (-)-4β,7α- and (-)-4α,7α-Aromadendranediols [J].

Carreras, Javier ;

Livendahl, Madeleine ;

McGonigal, Paul R. ;

Echavarren, Antonio M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (19) :4896-4899

[8] A Concise Total Synthesis of (-)-Maoecrystal Z [J].

Cha, Jacob Y. ;

Yeoman, John T. S. ;

Reisman, Sarah E. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (38) :14964-14967

[9] A Cascade Strategy Enables a Total Synthesis of (-)-Gephyrotoxin [J].

Chu, Shuyu ;

Wallace, Stephen ;

Smith, Martin D. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (50) :13826-13829

[10] Total Synthesis of the Protein Phosphatase 2A Inhibitor Lactodehydrothyrsiferol [J].

Clausen, Dane J. ;

Wan, Shuangyi ;

Floreancig, Paul E. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (22) :5178-5181

← 1 2 3 4 5 6 →