A simple, efficient access to functionalized pyrrolobenzazepines related to the ABC core of cephalotaxine

被引：16

作者：

deOliveira, ER ^{[1
]}

Dumas, F ^{[1
]}

dAngelo, J ^{[1
]}

机构：

[1] UNIV PARIS SUD,CTR ETUD PHARMACEUT,CNRS,UNITE CHIM ORGAN,F-92296 CHATENAY MALABR,FRANCE

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 21期

关键词：

D O I：

10.1016/S0040-4039(97)00709-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tetracyclic nitrile 19a and ester 19b, exhibiting the ABC core of cephalotaxine la, were prepared through KH-induced cyclization of thioimides 14a and 14b, respectively. This new ring-closure methodology proved to be particularly efficient: thus nitrile 19a was obtained in only 7 steps with a 17% overall yield from commercially available, inexpensive safrole 2. (C) 1997 Elsevier Science Ltd.

引用

页码：3723 / 3726

页数：4

共 7 条

[1] SYNTHESIS OF BIOACTIVE COMPOUNDS FROM ABUNDANT NATURAL PRODUCT .13. THE SYNTHESIS AND ANALGESIC PROPERTIES OF NEW SPIROISOCHROMANYL ACID-DERIVATIVES SYNTHESIZED FROM NATURAL SAFROLE [J].

CABRAL, LM ;

BARREIRO, EJ .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 32 (03) :959-962

[2] THIONATION REACTIONS OF LAWESSON REAGENTS [J].

CAVA, MP ;

LEVINSON, MI .

TETRAHEDRON, 1985, 41 (22) :5061-5087

[3] NEW ROUTES TO FUNCTIONALIZED BENZAZEPINE SUBSTRUCTURES - A NOVEL TRANSFORMATION OF AN ALPHA-DIKETONE THIOAMIDE INDUCED BY TRIMETHYL PHOSPHITE [J].

FANG, FG ;

MAIER, ME ;

DANISHEFSKY, SJ ;

SCHULTE, G .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (03) :831-838

[4] Two interrelated strategies for cephalotaxine synthesis [J].

Lin, XD ;

Kavash, RW ;

Mariano, PS .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (21) :7335-7347

[5]

LURIK BB, 1986, ZH ORG KHIM+, V22, P384

[6] CHIROSPECIFIC SYNTHESES OF (+)-ANATOXIN AND (-)-ANATOXIN-A [J].

PETERSEN, JS ;

FELS, G ;

RAPOPORT, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (16) :4539-4547

[7] A CONVENIENT PROCEDURE FOR BROMOMETHYLATION OF AROMATIC-COMPOUNDS - SELECTIVE MONOBROMOMETHYLATION, BISBROMOMETHYLATION, OR TRISBROMOMETHYLATION [J].

VANDERMADE, AW ;

VANDERMADE, RH .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (05) :1262-1263

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