APHIDICOLIN SYNTHESIS-(I) - FORMAL SYNTHESIS OF (+/-)-APHIDICOLIN BY THE SUCCESSIVE INTRAMOLECULAR DIELS-ALDER REACTIONS

被引:16
作者
TOYOTA, M [1 ]
NISHIKAWA, Y [1 ]
SEISHI, T [1 ]
FUKUMOTO, K [1 ]
机构
[1] TOHOKU UNIV,INST PHARMACEUT,SENDAI 98077,MIYAGI,JAPAN
关键词
D O I
10.1016/S0040-4020(01)81750-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Formal synthesis of an antitumor and antiviral diterpene aphidicolin (1) has been achieved. The key steps, 7-->6 and 4-->3, involve intramolecular Diels-Alder reaction.
引用
收藏
页码:10183 / 10192
页数:10
相关论文
共 31 条
[1]   A TOTAL SYNTHESIS OF APHIDICOLIN - STEREOSPECIFIC SYNTHESIS OF (+0-)-3-ALPHA,18-DIHYDROXY-17-NORAPHIDICOLAN-16-ONE [J].
BETTOLO, RM ;
TAGLIATESTA, P ;
LUPI, A ;
BRAVETTI, D .
HELVETICA CHIMICA ACTA, 1983, 66 (07) :1922-1928
[2]   ANTIVIRAL EFFECTS OF APHIDICOLIN, A NEW ANTIBIOTIC PRODUCED BY CEPHALOSPORIUM-APHIDICOLA [J].
BUCKNALL, RA ;
MOORES, H ;
SIMMS, R ;
HESP, B .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1973, 4 (03) :294-298
[3]  
BUNDRET KM, 1972, J CHEM SOC CHEM COMM, P1027
[4]   TOTAL SYNTHESIS OF (+/-)-APHIDICOLIN [J].
COREY, EJ ;
TIUS, MA ;
DAS, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (05) :1742-1744
[5]   STRUCTURE AND ABSOLUTE-CONFIGURATION OF ANTIBIOTIC APHIDICOLIN - TETRACYCLIC DITERPENOID CONTAINING A NEW RING-SYSTEM [J].
DALZIEL, W ;
HESP, B ;
STEVENSON, KM ;
JARVIS, JAJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (23) :2841-2851
[6]  
DOUROS J, 1980, NEW ANTICANCER DRUGS, P29
[7]   ENANTIOSELECTIVE TOTAL SYNTHESIS OF APHIDICOLIN [J].
HOLTON, RA ;
KENNEDY, RM ;
KIM, HB ;
KRAFFT, ME .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (05) :1597-1600
[8]   APHIDICOLIN PREVENTS MITOTIC CELL-DIVISION BY INTERFERING WITH ACTIVITY OF DNA POLYMERASE-ALPHA [J].
IKEGAMI, S ;
TAGUCHI, T ;
OHASHI, M .
NATURE, 1978, 275 (5679) :458-460
[9]   TOTAL SYNTHESIS OF (+/-)-APHIDICOLIN AND (+/-)-BETA-CHAMIGRENE [J].
IRELAND, RE ;
DOW, WC ;
GODFREY, JD ;
THAISRIVONGS, S .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (06) :1001-1013
[10]   AN EFFICIENT, STEREOSELECTIVE TOTAL SYNTHESIS OF (+/-)-APHIDICOLIN [J].
IRELAND, RE ;
GODFREY, JD ;
THAISRIVONGS, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (09) :2446-2448