Toward the synthesis of biologically important chlorins, isobacteriochlorins, and corrins. Cyclic enamides from acetylenic amides

被引:62
作者
Jacobi, PA
Brielmann, HL
Hauck, SI
机构
[1] Hall-Atwater Laboratories, Wesleyan University, Middletown
关键词
D O I
10.1021/jo960428+
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cyclic enamides 1 of a type useful in the synthesis of naturally occurring chlorins, isobacteriochlorins, and corrins have been prepared by a process involving 5-exo-dig cyclization of the appropriate acetylenic amides 11. The desired cyclization is catalyzed by either n-Bu(4)NF or LiAl-(NHBn)(4).
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页码:5013 / 5023
页数:11
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共 84 条
[31]  
GOSSAUER A, 1977, LIEBIGS ANN CHEM, P664
[32]  
Greene T.W., 1991, PROTECTIVE GROUPS OR, V2nd
[33]   SYNTHESIS OF GAMMA-LACTAM ANALOGS OF CARBAPENEMS WITH SUBSTITUTED-THIO GROUPS AT THE C-3 POSITION [J].
HASHIGUCHI, S ;
NATSUGARI, H ;
OCHIAI, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (08) :2345-2352
[34]   FACILE SYNTHESIS OF ALPHA,BETA-UNSATURATED NIOBIUM ACYLS VIA GAMMA-HYDRIDE ABSTRACTION [J].
HNEIHEN, AS ;
FERMIN, MC ;
MAAS, JJ ;
BRUNO, JW .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1992, 429 (03) :C33-C37
[35]   The conditions underlying the formation of unsaturated and of cyclic compounds from halogenated open-chain derivatives Part I Products derived from a-halogenated glutaric acids [J].
Ingold, CK .
JOURNAL OF THE CHEMICAL SOCIETY, 1921, 119 :305-329
[36]   PYRROLES AND RELATED COMPOUNDS .17. PORPHYRIN SYNTHESIS THROUGH B-BILENES [J].
JACKSON, AH ;
KENNER, GW ;
SMITH, KM .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (03) :502-&
[37]  
JACOBI P, 1996, IN PRESS J ORG CHEM, V61
[38]   A NOVEL SYNTHESIS OF PYRROMETHENONES [J].
JACOBI, PA ;
BUDDHU, SC .
TETRAHEDRON LETTERS, 1988, 29 (38) :4823-4826
[39]   TETRAPYRROLES .3. HOMOCHIRAL DIHYDROPYRROMETHENONES FROM N-AMINOPYRROLES AND ACETYLENIC ACIDS [J].
JACOBI, PA ;
RAJESWARI, S .
TETRAHEDRON LETTERS, 1992, 33 (42) :6231-6234
[40]  
JACOBI PA, 1993, HETEROCYCLES, V35, P1103