Simple synthesis of two naphthoquinone antibiotics psychorubrin and pentalongin

被引:8
作者
Bulbule, VJ [1 ]
Koranne, PS [1 ]
Munot, YS [1 ]
Borate, HB [1 ]
Deshpande, VH [1 ]
机构
[1] Natl Chem Lab, Div Organ Chem Technol, Pune 411008, Maharashtra, India
关键词
D O I
10.1081/SCC-120015812
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1H-Naphtho[2,3-c]pyran-5,10-dione derivatives were synthesized using chloromethylation of substituted-2-naphthylacetic acid as the key step. The utility of this method was demonstrated in the synthesis of two-pyranonaphthoquinone antibiotics psychorubrin (1) and pentalongin (2).
引用
收藏
页码:587 / 594
页数:8
相关论文
共 20 条
[1]  
De Kimpe N., 2001, TETRAHEDRON, V57, P4213
[2]  
FINKELSTEIN J, 1976, ORG SYNTH, V55, P45
[3]   NAPHTHOQUINOID PIGMENTS FROM PENTAS-LONGIFLORA [J].
HARI, L ;
DEBUYCK, LF ;
DEPOOTER, HL .
PHYTOCHEMISTRY, 1991, 30 (05) :1726-1727
[4]   ANTITUMOR AGENTS .89. PSYCHORUBRIN, A NEW CYTOTOXIC NAPHTHOQUINONE FROM PSYCHOTRIA RUBRA AND ITS STRUCTURE-ACTIVITY-RELATIONSHIPS [J].
HAYASHI, T ;
SMITH, FT ;
LEE, KH .
JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (11) :2005-2008
[5]   PRODUCTION OF DEOXYFRENOLICIN AND A NEW ANTIBIOTIC, FRENOLICIN-B BY STREPTOMYCES-ROSEOFULVUS STRAIN AM-3867 [J].
IWAI, Y ;
KORA, A ;
TAKAHASHI, Y ;
HAYASHI, T ;
AWAYA, J ;
MASUMA, R ;
OIWA, R ;
OMURA, S .
JOURNAL OF ANTIBIOTICS, 1978, 31 (10) :959-965
[6]   THE SYNTHESIS OF RADERMACHOL [J].
JOSHI, BS ;
JIANG, QP ;
RHO, T ;
PELLETIER, SW .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (26) :8220-8232
[7]   ISOLATION AND CHARACTERIZATION OF NAPHTHAQUINONE PIGMENTS FROM TORULA-HERBARUM (PERS) HERBARIN AND DEHYDROHERBARIN [J].
KADKOL, MV ;
GOPALKRISHNAN, KS ;
NARASIMHACHARI, N .
JOURNAL OF ANTIBIOTICS, 1971, 24 (04) :245-+
[8]   Synthesis of two naphthoquinone antibiotics, dehydroherbarin and 6-deoxybostrycoidin [J].
Kesteleyn, B ;
De Kimpe, N .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (03) :640-644
[9]   Total synthesis of two naphthoquinone antibiotics, psychorubrin and pentalongin, and their C(1)-substituted alkyl and aryl derivatives [J].
Kesteleyn, B ;
De Kimpe, N ;
Van Puyvelde, L .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (04) :1173-1179
[10]   Synthesis of 1H-2-naphtho[2,3-c]thiapyran-5,10-dione-2,2-dioxide, a 2-sulfone analogue of pentalongin [J].
Kesteleyn, B ;
De Kimpe, N .
TETRAHEDRON LETTERS, 2000, 41 (05) :755-758