A REMARKABLY SIMPLE, HIGHLY EFFICIENT, AND STEREOSELECTIVE SYNTHESIS OF STEROIDS AND OTHER POLYCYCLIC SYSTEMS - TOTAL SYNTHESIS OF ESTRA-1,3,5(10)-TRIEN-17-ONE VIA INTRAMOLECULAR CAPTURE OF ORTHO-QUINODIMETHANES GENERATED BY CHELETROPIC ELIMINATION OF SO2

被引:137
作者
NICOLAOU, KC
BARNETTE, WE
MA, P
机构
关键词
D O I
10.1021/jo01296a023
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
引用
收藏
页码:1463 / 1470
页数:8
相关论文
共 20 条
[1]   CONDENSED CYCLOBUTANE AROMATIC COMPOUNDS .13. AN ATTEMPTED SYNTHESIS OF 1,2-DIPHENYLBENZOCYCLOBUTENE [J].
CAVA, MP ;
MITCHELL, MJ ;
DEANA, AA .
JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (09) :1481-1484
[2]   CONDENSED CYCLOBUTANE AROMATIC COMPOUNDS .6. THE PYROLYSIS OF 1,3-DIHYDROISOTHIANAPHTHENE-2,2-DIOXIDE - A NEW SYNTHESIS OF BENZOCYCLOBUTENE [J].
CAVA, MP ;
DEANA, AA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (16) :4266-4268
[3]   INSITU GENERATION AND INTRAMOLECULAR TRAPPING OF OMICRON-XYLYLENES BY COBALT-CATALYZED ACETYLENE COOLIGOMERIZATIONS - ONE-STEP SYNTHESIS OF POLYCYCLES [J].
FUNK, RL ;
PETER, K ;
VOLLHARDT, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (21) :6755-6757
[4]   COBALT-CATALYZED STEROID SYNTHESIS [J].
FUNK, RL ;
VOLLHARDT, KPC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (16) :5483-5484
[5]   COBALT WAY TO DL-ESTRONE, A HIGHLY REGIOSPECIFIC FUNCTIONALIZATION OF 2,3-BIS(TRIMETHYLSILYL)ESTRATRIEN-17-ONE [J].
FUNK, RL ;
VOLLHARDT, KPC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (01) :215-217
[6]   SYNTHESIS AND SOLVOLYSIS OF DERIVATIVES OF 7-METHYL-7-HYDROXYNORBORNANE AND EPIMERIC 7-METHYL-7-HYDROXYNORBORNENES [J].
GASSMAN, PG ;
PASCONE, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (23) :7801-7813
[7]   SUBSTITUTED BENZOCYCLOBUTENES, INDANS, AND TETRALINS VIA COBALT-CATALYZED COOLIGOMERIZATION OF ALPHA,OMEGA-DIYNES WITH SUBSTITUTED ACETYLENES - FORMATION AND SYNTHETIC UTILITY OF TRIMETHYLSILYLATED BENZOCYCLOALKENES [J].
HILLARD, RL ;
VOLLHARDT, KPC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (12) :4058-4069
[8]   ASYMMETRIC TOTAL SYNTHESIS OF ESTRADIOL BY AN INTRA-MOLECULAR CYCLOADDITION OF BENZOCYCLOBUTENE DERIVATIVE [J].
KAMETANI, T ;
MATSUMOTO, H ;
NEMOTO, H ;
FUKUMOTO, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (19) :6218-6220
[9]   COMPETITIVE REACTIONS BETWEEN SIGMATROPIC REACTION AND CYCLOADDITION AFFECTED BY GEOMETRY OF ORTHO-QUINODIMETHANES [J].
KAMETANI, T ;
TSUBUKI, M ;
SHIRATORI, Y ;
KATO, Y ;
NEMOTO, H ;
IHARA, M ;
FUKUMOTO, K ;
SATOH, F ;
INOUE, H .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (16) :2672-2676
[10]  
KAMETANI T, 1977, J AM CHEM SOC, V99, P3401