Formal total synthesis of (±)-vindoline by tandem radical cyclization

被引:55
作者
Zhou, SZ [1 ]
Bommezijn, S [1 ]
Murphy, JA [1 ]
机构
[1] Univ Strathclyde, Dept Pure & Appl Chem, Glasgow G1 1XL, Lanark, Scotland
关键词
D O I
10.1021/ol0171618
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A formal total synthesis of (+/-)-vindoline 1 has been achieved featuring the tandem cyclization of radicals produced from the iodoaryl azide 19a.
引用
收藏
页码:443 / 445
页数:3
相关论文
共 18 条
[1]   TOTAL SYNTHESIS OF (+/-)-VINDOLINE [J].
ANDO, M ;
BUCHI, G ;
OHNUMA, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (23) :6880-6881
[2]   A NEW EFFICIENT TOTAL SYNTHESIS OF VINDOROSINE AND VINDOLINE [J].
ANDRIAMIALISOA, RZ ;
LANGLOIS, N ;
LANGLOIS, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (07) :961-967
[3]  
BAN Y, 1978, TETRAHEDRON LETT, P151
[4]   ASPIDOSPERMA ALKALOIDS - CONVERSION OF TABERSONINE INTO VINDOLINE [J].
DANIELI, B ;
LESMA, G ;
PALMISANO, G ;
RIVA, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (01) :155-161
[5]   RAPID ACCESS TO THE HIGHLY OXYGENATED ASPIDOSPERMA ALKALOIDS VINDOLINE, VINDOROSINE, AND CATHOVALINE [J].
DANIELI, B ;
LESMA, G ;
PALMISANO, G ;
RIVA, R .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (14) :909-911
[6]   SYNTHESIS OF (-)-VINDOLINE [J].
FELDMAN, PL ;
RAPOPORT, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (05) :1603-1604
[7]   SYNTHETIC STUDIES ON POLYETHER ANTIBIOTICS .5. TOTAL SYNTHESIS OF MONENSIN .2. STEREOCONTROLLED SYNTHESIS OF THE RIGHT HALF OF MONENSIN [J].
FUKUYAMA, T ;
WANG, CLJ ;
KISHI, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (01) :260-262
[8]   VINCA ALKALOIDS .10. STRUCTURE OF VINDOLINE [J].
GORMAN, M ;
NEUSS, N ;
BIEMANN, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (06) :1058-&
[9]   NOVEL RADICAL CYCLIZATIONS OF ALKYL AZIDES - A NEW ROUTE TO N-HETEROCYCLES [J].
KIM, S ;
JOE, GH ;
DO, JY .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (12) :5521-5522
[10]   Tandem radical cyclizations on iodoaryl azides:: Synthesis of the core tetracycle of Aspidosperma alkaloids [J].
Kizil, M ;
Patro, B ;
Callaghan, O ;
Murphy, JA ;
Hursthouse, HB ;
Hibbs, D .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (21) :7856-7862