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
[11]   SYNTHESIS AND IN-VITRO ACTIVITY OF 17-BETA-((N-ALKYL/ARYLFORMAMIDO)-4-METHYL-4-AZA-3-OXO-5-ALPHA-ANDROSTAN-3-ONES AND 17-BETA-[(N-ALKYL/ARYL)ALKYL/ARYLAMIDO]-4-METHYL-4-AZA-3-OXO-5-ALPHA-ANDROSTAN-3-ONES AS INHIBITORS OF HUMAN 5-ALPHA-REDUCTASES AND ANTAGONISTS OF THE ANDROGEN RECEPTOR [J].
LI, X ;
SINGH, SM ;
LABRIE, F .
JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (07) :1158-1173
[12]  
MORZYCKI JW, 1995, POL J CHEM, V69, P321
[13]   CARBON-CARBON BOND-FORMING REACTIONS OF ZINC HOMOENOLATE OF ESTERS - A NOVEL 3-CARBON NUCLEOPHILE WITH GENERAL SYNTHETIC UTILITY [J].
NAKAMURA, E ;
AOKI, S ;
SEKIYA, K ;
OSHINO, H ;
KUWAJIMA, I .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (26) :8056-8066
[14]   Cascade radical processes leading to polycycle constructions. The total synthesis of spongian-16-one [J].
Pattenden, G ;
Roberts, L .
TETRAHEDRON LETTERS, 1996, 37 (24) :4191-4194
[15]   Biomimetic cyclization of enamide-containing polyenes as a new route to azapolycycles [J].
Sen, SE ;
Roach, SL .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (19) :6646-6650
[16]   STEROIDS AND RELATED STUDIES .25. CHANDONIUM IODIDE (17A-METHYL-3 BETA-PYRROLIDINO-17A-AZA-D-HOMOANDROST-5-ENE DIMETHIODIDE) AND OTHER QUATERNARY AMMONIUM STEROID ANALOGS [J].
SINGH, H ;
PAUL, D .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (12) :1475-1479