SYNTHESES OF 1-SUBSTITUTED 12-OXAHEXACYCLO[7.2.1.0(2,8).0(3,7).0(4,11).0(6,10)]DODECANES AND THEIR TRANSFORMATION INTO PENTACYCLO[6.3.0.0(2,6).0(3,10).0(5,9)]UNDECANE DERIVATIVES

被引:6
作者
ALEKSANDROV, AM
KASHYAP, RP
PEHK, TJ
PETRENKO, AE
WATSON, WH
机构
[1] ESTONIAN ACAD SCI,INST CHEM & BIOL PHYS,TALLINN 200001,ESTONIA
[2] TEXAS CHRISTIAN UNIV,DEPT CHEM,FT WORTH,TX 76129
关键词
D O I
10.1021/jo00059a039
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of nucleophilic reagents (organomagnesium and organosodium compounds containing active methylene groups) with exo-11-bromopentacyclo[5.4.0.0(2,6).0(3,10).0(5,9)]undecan-8-one leads to the formation of 1-substituted-12-oxahexacyclo[7.2.1.0(2,8).0(3,7).0(4,11).0(6,10)] dodecanes which can be used in the synthesis of trishomocubane derivatives. It is shown, using the 1-methyl- and 1-phenyl-substituted 12-oxadodecanes, that iodotrimethylsilane readily cleaves the ether bond at C(l). The resulting carbonium ions rearrange to form 1,7,11-trisubstituted pentacyclo[6.3.0.0(2,6).0(3,10).0(5,9)]-undecanes.
引用
收藏
页码:1831 / 1834
页数:4
相关论文
共 22 条
[12]   REDUCTIVE AMINATION OF PENTACYCLO[5.4.0.0/2,6/0/3,10/0/5,9]UNDECANE-8,11-DIONE [J].
MARCHAND, AP ;
DAVE, PR ;
SATYANARAYANA, N ;
ARNEY, BE .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (05) :1088-1092
[13]   FACILE STEREOSELECTIVE REDUCTIONS OF ENEDIONES AND CAGE DIKETONES USING NABH4-CECL3 [J].
MARCHAND, AP ;
LAROE, WD ;
SHARMA, GVM ;
SURI, SC ;
REDDY, DS .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (09) :1622-1625
[14]  
MARCHAND AP, 1989, CHEM REV, V89, P1041
[15]  
MEINWALD J, 1965, ORG SYN, V45, P77
[16]   SELECTIVE AND STEREOSPECIFIC HORSE LIVER ALCOHOL DEHYDROGENASE-CATALYZED REDUCTION OF CAGE-SHAPED MESO-DIKETONE - AN EFFICIENT ACCESS TO OPTICALLY-ACTIVE D3-TRISHOMOCUBANE DERIVATIVE [J].
NAEMURA, K ;
FUJII, T ;
CHIKAMATSU, H .
CHEMISTRY LETTERS, 1986, (06) :923-926
[17]   SYNTHESIS AND PHOTOPHYSICAL PROPERTIES OF SOME ENDO-6-SUBSTITUTED NORCAMPHORS AND PENTACYCLO[5.4.0.02,6.03,10.05,9]UNDECAN-8-ONES [J].
SAUERS, RR ;
ZAMPINO, M ;
STOCKL, M ;
FERENTZ, J ;
SHAMS, H .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (11) :1862-1866
[18]   SYNTHESIS AND PHOTOCHEMISTRY OF SOME NEW PENTACYCLOUNDECAN-8-ONES - PROBES FOR HYDROGEN ABSTRACTION IN THE PI-PLANE [J].
SAUERS, RR ;
SCIMONE, A ;
SHAMS, H .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (26) :6084-6089
[19]   SYNTHESES OF PENTACYCLO[6.3.0.02,6.03,10.05,9]UNDECYL (TRISHOMOCUBYL) AND TETRACYCLO[6.3.0.04,11.05,9]UNDECA-2,6-DIENYL (HOMOHYPOSTROPHENYL) SYSTEMS [J].
SMITH, EC ;
BARBORAK, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (08) :1433-1437
[20]   PYRAMIDALIZATION IN A HEXACHLORONORBORNADIENE DERIVATIVE [J].
WATSON, WH ;
KASHYAP, RP ;
PLUMMER, BF .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1991, 47 :584-587