How to 'Cope' with the Prenylation of the Indole C4 Position

被引：19

作者：

Schwarzer, Darius D. ^{[1
]}

Gritsch, Philipp J. ^{[1
]}

Gaich, Tanja ^{[1
]}

机构：

[1] Leibniz Univ Hannover, Inst Organ Chem, Dept Chem, D-30167 Hannover, Germany

来源：

SYNLETT | 2013年 / 24卷 / 09期

关键词：

biomimetic synthesis; biosynthesis; pericyclic reaction; enzymes; alkaloids; ERGOT ALKALOID BIOSYNTHESIS; ELECTROPHILIC SUBSTITUTION; CHORISMATE MUTASE; DIMETHYLALLYLTRYPTOPHAN SYNTHASE; TRANSITION-STATE; CATALYZED REARRANGEMENT; WELWITINDOLINONES; ISONITRILE; ECHINULIN; ENZYME;

D O I：

10.1055/s-0032-1318501

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Evidence supporting an enzyme-catalyzed [3,3]-sigmatropic rearrangement of the dimethallylltryptophan synthase is highlighted. A bioinspired system is discussed, by which the chemical feasibility of Cope rearrangement to the 4-position of the indole nucleus was accomplished. Furthermore, synthesis of the tricyclic benzo[cd]indole core of welwitindolinones and dragmacidine E is presented.

引用

页码：1025 / 1031

页数：7

共 65 条

[41]

PACHLATKO P, 1975, CHIMIA, V29, P526

[42]

Plieninger H., 1967, LIEBIGS ANN CHEM, P706

[43] Mechanistic Studies on CymD: A Tryptophan Reverse N-Prenyltransferase [J].

Qian, Qi ;

Schultz, Andrew W. ;

Moore, Bradley S. ;

Tanner, Martin E. .

BIOCHEMISTRY, 2012, 51 (39) :7733-7739

[44] Total Synthesis of Oxidized Welwitindolinones and (-)-N-Methylwelwitindolinone C Isonitrile [J].

Quasdorf, Kyle W. ;

Huters, Alexander D. ;

Lodewyk, Michael W. ;

Tantillo, Dean J. ;

Garg, Neil K. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (03) :1396-1399

[45] The lyngbyatoxin biosynthetic assembly line: Chain release by four-electron reduction of a dipeptidyl thioester to the corresponding alcohol [J].

Read, Jay A. ;

Walsh, Christopher T. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (51) :15762-+

[46] Total synthesis of (±)-welwitindolinone A isonitrile [J].

Reisman, SE ;

Ready, JM ;

Hasuoka, A ;

Smith, CJ ;

Wood, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (05) :1448-1449

[47] Enantiospecific Total Synthesis of the Hapalindoles, Fischerindoles, and Welwitindolinones via a Redox Economic Approach [J].

Richter, Jeremy M. ;

Ishihara, Yoshihiro ;

Masuda, Takeshi ;

Whitefield, Brandon W. ;

Llamas, Tomas ;

Pohjakallio, Antti ;

Baran, Phil S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (52) :17938-17954

[48] Total synthesis of (+)-okaramine J featuring an exceptionally facile N-reverse-prenyl to C-prenyl Aza-Claisen rearrangement [J].

Roe, JM ;

Webster, RAB ;

Ganesan, A .

ORGANIC LETTERS, 2003, 5 (16) :2825-2827

[49] ZINC CHLORIDE CATALYZED, THERMAL REARRANGEMENTS OF N-ALLYLANILINES AND C-ALLYLANILINES - CHARGE INDUCED AND AROMATIC AMINO CLAISEN REARRANGEMENTS [J].

SCHMID, M ;

HANSEN, HJ ;

SCHMID, H .

HELVETICA CHIMICA ACTA, 1973, 56 (01) :105-124

[50] Mimicking Dimethylallyltryptophan Synthase: Experimental Evidence for a Biosynthetic Cope Rearrangement Process [J].

Schwarzer, Darius D. ;

Gritsch, Philipp J. ;

Gaich, Tanja .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (46) :11514-11516

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