Strategies for the Total Synthesis of Clavicipitic Acid

被引：36

作者：

Ito, Mamoru ^{[1
]}

Tahara, Yu-ki ^{[1
]}

Shibata, Takanori ^{[1
,2
]}

机构：

[1] Waseda Univ, Sch Adv Sci & Engn, Dept Chem & Biochem, Shinjuku Ku, Tokyo 1698555, Japan

[2] ACT C Japan Sci & Technol Agcy JST, 4-1-8 Honcho Kawaguchi, Saitama 3320012, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 16期

关键词：

azepinoindole; clavicipitic acid; gramine; total synthesis; tryptophan; ERGOT ALKALOIDS; ENANTIOSELECTIVE SYNTHESIS; (-)-CIS-CLAVICIPITIC ACID; BIOMIMETIC SYNTHESIS; FORMAL SYNTHESIS; 3-STEP SYNTHESIS; METHYL-ESTER; INDOLES; CHEMISTRY; BIOSYNTHESIS;

D O I：

10.1002/chem.201505014

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Clavicipitic acid is an ergot alkaloid, which was isolated from Claviceps strain and Claviceps fusiformis. Its unique tricyclic azepinoindole skeleton has attracted synthetic chemists, and various strategies have been developed for its total synthesis. These strategies can be generally categorized into two types based on the synthetic intermediates, namely, 4-substituted gramine derivatives and 4-substituted tryptophan derivatives. This Minireview summarizes the reported total syntheses from the point of these two key intermediates

引用

页码：5468 / 5477

页数：10

共 48 条

[1] An efficient route to the alpha-methyl ester of L-glutamic acid, and its conversion into cis-5-hydroxy-L-pipecolic acid [J].

Adams, DR ;

Bailey, PD ;

Collier, ID ;

Heffernan, JD ;

Stokes, S .

CHEMICAL COMMUNICATIONS, 1996, (03) :349-350

[2] Synthesis of (±)-cis-Clavicipitic Acid by a Rh(I)-Catalyzed Intramolecular Imine Reaction [J].

Bartoccini, Francesca ;

Casoli, Mariangela ;

Mari, Michele ;

Piersanti, Giovanni .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (07) :3255-3259

[3] FORMAL SYNTHESIS OF CLAVICIPITIC ACID BASED ON A BIOSYNTHETIC PROPOSAL [J].

BOYLES, DA ;

NICHOLS, DE .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (21) :5128-5130

[4] BIOSYNTHESIS OF ERGOT ALKALOIDS AND RELATED COMPOUNDS [J].

FLOSS, HG .

TETRAHEDRON, 1976, 32 (08) :873-912

[5] PALLADIUM-CATALYZED REACTIONS IN THE SYNTHESIS OF 3-SUBSTITUTED AND 4-SUBSTITUTED INDOLES .2. TOTAL SYNTHESIS OF THE N-ACETYL METHYL-ESTER OF (+/-)-CLAVICIPITIC ACIDS [J].

HARRINGTON, PJ ;

HEGEDUS, LS ;

MCDANIEL, KF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (14) :4335-4338

[6] A concise total synthesis of (+/-)-cis- and (+/-)-trans-clavicipitic acids by combinational use of directed lithiation and fluoride ion-induced elimination-addition reaction of 1-(triisopropylsilyl)gramine derivatives [J].

Iwao, M ;

Ishibashi, F .

TETRAHEDRON, 1997, 53 (01) :51-58

[7] Palladium-catalyzed, modular synthesis of highly functionalized indoles and tryptophans by direct annulation of substituted o-haloanilines and aldehydes [J].

Jia, Yanxing ;

Zhu, Jieping .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (20) :7826-7834

[8] STRUCTURE OF CLAVICIPITIC ACID, AN AZEPINOINDOLE DERIVATIVE FROM CLAVICEPS-FUSIFORMIS [J].

KING, GS ;

WAIGHT, ES ;

MANTLE, PG ;

SZCZYRBAK, CA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (19) :2099-2103

[9]

KING GS, 1973, TETRAHEDRON LETT, P215

[10] A BIOMIMETIC ROUTE TO THE ERGOT DERAILMENT PRODUCTS, THE CLAVICIPITIC ACIDS - DETECTION OF A REACTIVE INTERMEDIATE BY P-31 NMR - SOME CHEMICAL UNDERPINNINGS FOR A PROPOSED INTERMEDIATE IN ERGOT ALKALOID BIOSYNTHESIS [J].

KOZIKOWSKI, AP ;

OKITA, M .

TETRAHEDRON LETTERS, 1985, 26 (34) :4043-4046

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