A concise synthesis of (±)-methylenolactocin and the formal synthesis of (±)-phaseolinic acid

被引:38
作者
Loh, TP [1 ]
Lye, PL [1 ]
机构
[1] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
关键词
D O I
10.1016/S0040-4039(01)00492-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(+/-)-Methylenolactocin was prepared in five steps involving an indium-mediated allylation reaction as the key step. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3511 / 3514
页数:4
相关论文
共 20 条
[1]   PREPARATION AND SOME REACTIONS OF ALLYLIC INDIUM REAGENTS [J].
ARAKI, S ;
SHIMIZU, T ;
JOHAR, PS ;
JIN, SJ ;
BUTSUGAN, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) :2538-2542
[2]   NOVEL, ENANTIOSELECTIVE LACTONE CONSTRUCTION - 1ST SYNTHESIS OF METHYLENOLACTOCIN, ANTITUMOR ANTIBIOTIC FROM PENICILLIUM SP [J].
DEAZEVEDO, MBM ;
MURTA, MM ;
GREENE, AE .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (17) :4567-4569
[3]   HELENANOLIDES - STEREOCONTROLLED TOTAL SYNTHESIS OF DL-BIGELOVIN, DL-MEXICANIN-I, AND DL-LINIFOLIN-A [J].
GRIECO, PA ;
OHFUNE, Y ;
MAJETICH, GF .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (03) :360-366
[4]  
Heathcock C. L., 1983, TOTAL SYNTHESIS NATU, V5
[5]   SYNTHESIS AND BIOLOGICAL-ACTIVITY OF ALPHA-METHYLENE-GAMMA-BUTYROLACTONES [J].
HOFFMANN, HMR ;
RABE, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (02) :94-110
[6]   AN ENANTIOSELECTIVE SYNTHESIS OF 3,4-DISUBSTITUTED BUTYROLACTONES [J].
HONDA, T ;
KIMURA, N .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (01) :77-78
[7]   Organic syntheses using indium-mediated and catalyzed reactions in aqueous media [J].
Li, CJ ;
Chan, TH .
TETRAHEDRON, 1999, 55 (37) :11149-11176
[8]   Studies towards total synthesis of antillatoxin: Synthesis of C1-C11 fragment [J].
Loh, TP ;
Cao, GQ ;
Pei, J .
TETRAHEDRON LETTERS, 1998, 39 (11) :1457-1460
[9]  
LOH TP, 1996, SYNLETT, P263
[10]   STRUCTURE AND STEREOCHEMISTRY OF PHASEOLINIC ACID - A NEW ACID FROM MACROPHOMINA-PHASEOLINA [J].
MAHATO, SB ;
SIDDIQUI, KAI ;
BHATTACHARYA, G ;
GHOSAL, T ;
MIYAHARA, K ;
SHOLICHIN, M ;
KAWASAKI, T .
JOURNAL OF NATURAL PRODUCTS, 1987, 50 (02) :245-247