New Route to the Ergoline Skeleton via Cyclization of 4-Unsubstituted Indoles

被引：10

作者：

Burley, Scott D. ^{[1
]}

Lam, Vicky V. ^{[2
]}

Lakner, Frederick J. ^{[2
]}

Bergdahl, B. Mikael ^{[1
]}

Parker, Matthew A. ^{[1
]}

机构：

[1] San Diego State Univ, Dept Chem, San Diego, CA 92182 USA

[2] ChemDiv Inc, San Diego, CA 92121 USA

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 11期

基金：

美国国家卫生研究院;

关键词：

LYSERGIC-ACID; (+)-LYSERGIC ACID; ERGOT ALKALOIDS; CHLORIDE;

D O I：

10.1021/ol400620a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new route to the ergoline skeleton has been developed that does not require prior functionalization of the indole 4-position. The indole nucleus is introduced late in the synthesis to allow for eventual efficient introduction of substituents in this region. Key steps include Negishi coupling of a three-carbon chain to a bromonicotinate ester, Fischer indole synthesis to facilitate incorporation of substituents via phenylhydrazines, and Pd-catalyzed cyclization to form the ergoline C ring.

引用

页码：2598 / 2600

页数：3

共 25 条

[11] A new synthesis of lysergic acid [J].

Hendrickson, JB ;

Wang, J .

ORGANIC LETTERS, 2004, 6 (01) :3-5

[12] Synthesis of 1,8-naphthyridine C-nucleosides and their base-pairing properties in oligodeoxynucleotides:: Thermally stable Naphthyridine:Imidazopyridopyrimidine base-pairing motifs [J].

Hikishima, S ;

Minakawa, N ;

Kuramoto, K ;

Fujisawa, Y ;

Ogawa, M ;

Matsuda, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (04) :596-598

[13] 2-chloro-1,3-dimethylimidazolinium chloride. 1. A powerful dehydrating equivalent to DCC [J].

Isobe, T ;

Iskikawa, T .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (19) :6984-6988

[14]

JAEHNE G, 2008, Patent No. 2008017381

[15] THE TOTAL SYNTHESIS OF LYSERGIC ACID [J].

KORNFELD, EC ;

FORNEFELD, EJ ;

KLINE, GB ;

MANN, MJ ;

MORRISON, DE ;

JONES, RG ;

WOODWARD, RB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (13) :3087-3114

[16] New phenanthridine linkers for the solid-phase synthesis of acid-containing compounds [J].

Li, WR ;

Lin, YS ;

Hsu, NM .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2001, 3 (06) :634-643

[17] Total Synthesis of (+)-Lysergic Acid [J].

Liu, Qiang ;

Jia, Yanxing .

ORGANIC LETTERS, 2011, 13 (18) :4810-4813

[18] AN EXTENDED TABLE OF HAMMETT SUBSTITUENT CONSTANTS BASED ON THE IONIZATION OF SUBSTITUTED BENZOIC ACIDS [J].

MCDANIEL, DH ;

BROWN, HC .

JOURNAL OF ORGANIC CHEMISTRY, 1958, 23 (03) :420-427

[19] Enantioefficient synthesis of α-ergocryptine:: First direct synthesis of (+)-lysergic acid [J].

Moldvai, I ;

Temesvári-Major, E ;

Incze, M ;

Szentirmay, K ;

Gács-Baitz, E ;

Szántay, C .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (18) :5993-6000

[20] PALLADIUM-CATALYZED OR NICKEL-CATALYZED CROSS COUPLING - A NEW SELECTIVE METHOD FOR CARBON CARBON BOND FORMATION [J].

NEGISHI, EI .

ACCOUNTS OF CHEMICAL RESEARCH, 1982, 15 (11) :340-348

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