Cascade radical cyclisations involving enamide double bonds. A synthetic approach to azasteroids

被引:13
作者
Double, P [1 ]
Pattenden, G [1 ]
机构
[1] Univ Nottingham, Dept Chem, Nottingham NG7 2RD, England
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 13期
关键词
D O I
10.1039/a802298d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of the enamide selenoesters 8 and 14 with Bu3SnH-AIBN is shown to lead to the nitrogen tricycle 9 (63%) and the D-homo-12-azasteroid 16 (45%) respectively, by way of serial stereoselective 6-endo-trig radical cyclisations.
引用
收藏
页码:2005 / 2007
页数:3
相关论文
共 16 条
[1]   Synthesis of heterocycles by radical cyclisation [J].
Aldabbagh, F ;
Bowman, WR .
CONTEMPORARY ORGANIC SYNTHESIS, 1997, 4 (04) :261-280
[2]   Acyl radical-mediated polyene cyclisations directed towards steroid ring synthesis [J].
Batsanov, A ;
Chen, LG ;
Gill, GB ;
Pattenden, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (01) :45-55
[3]   Cascade radical cyclisations of imines [J].
Bowman, WR ;
Stephenson, PT ;
Young, AR .
TETRAHEDRON, 1996, 52 (35) :11445-11462
[4]   Consecutive-6-endo trigonal cyclisations from polyene acyl radical intermediates leading to decalone and perhydrophenanthrone ring constructions [J].
Chen, LG ;
Gill, GB ;
Pattenden, G ;
Simonian, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (01) :31-43
[5]   SYNTHESIS OF ANTIFUNGAL ANTIBIOTIC A25822 FACTOR-A [J].
DOLLE, RE ;
KRUSE, LI .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (02) :133-135
[6]   DESIGN AND SYNTHESIS OF 14-ALPHA-METHYL-15-AZA-D-HOMOSTEROLS AS NOVEL ANTIMYCOTICS [J].
DOLLE, RE ;
ALLAUDEEN, HS ;
KRUSE, LI .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (02) :877-880
[7]   Free radical cyclizations involving nitrogen [J].
Fallis, AG ;
Brinza, IM .
TETRAHEDRON, 1997, 53 (52) :17543-17594
[8]   6-AZASTEROIDS - STRUCTURE-ACTIVITY-RELATIONSHIPS FOR INHIBITION OF TYPE-1 AND TYPE-2 HUMAN 5-ALPHA-REDUCTASE AND HUMAN ADRENAL 3-BETA-HYDROXY-DELTA(5)-STEROID DEHYDROGENASE 3-KETO-DELTA(5)-STEROID ISOMERASE [J].
FRYE, SV ;
HAFFNER, CD ;
MALONEY, PR ;
MOOK, RA ;
DORSEY, GF ;
HINER, RN ;
CRIBBS, CM ;
WHEELER, TN ;
RAY, JA ;
ANDREWS, RC ;
BATCHELOR, KW ;
BRAMSON, HN ;
STUART, JD ;
SCHWEIKER, SL ;
VANARNOLD, J ;
CROOM, S ;
BICKETT, DM ;
MOSS, ML ;
TIAN, GC ;
UNWALLA, RJ ;
LEE, FW ;
TIPPIN, TK ;
JAMES, MK ;
GRIZZLE, MK ;
LONG, JE ;
SCHUSTER, SV .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (15) :2352-2360
[9]   NEW AZASTEROIDAL ANTIFUNGAL ANTIBIOTICS FROM GEOTRICHUM-FLAVO-BRUNNEUM .3. BIOLOGICAL-ACTIVITY [J].
GORDEE, RS ;
BUTLER, TF .
JOURNAL OF ANTIBIOTICS, 1975, 28 (02) :112-117
[10]   A new approach to steroid ring construction based on a novel radical cascade sequence [J].
Handa, S ;
Pattenden, G ;
Li, WS .
CHEMICAL COMMUNICATIONS, 1998, (03) :311-312