A NOVEL REARRANGEMENT OF CYCLOBUTANES TO CYCLOPROPANES - CONSTRUCTION OF TRICYCLO[5.4.0.01,3]UNDECANE AND BICYCLO[4.1.0]HEPTANE SYSTEMS

被引：6

作者：

IHARA, M ^{[1
]}

TANIGUCHI, T ^{[1
]}

TANIGUCHI, N ^{[1
]}

FUKUMOTO, K ^{[1
]}

机构：

[1] TOHOKU UNIV,INST PHARMACEUT,SENDAI,MIYAGI 980,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1993年 / 19期

关键词：

D O I：

10.1039/c39930001477

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Treatment of hydroxylated cyclobutane derivatives with BF3.OEt2, POCl3 in the presence of pyridine or Raney nickel causes a novel rearrangement forming tricyclo[5.4.0.0(1,3)]undecane and bicyclo[4.1.0]heptane systems.

引用

页码：1477 / 1479

页数：3

共 14 条

[1] SYNTHESIS AND CONVERSION OF PRESQUALENE ALCOHOL TO SQUALENE [J].

ALTMAN, LJ ;

KOWERSKI, RC ;

RILLING, HC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (07) :1782-&

[2]

BARNIER JP, 1976, B SOC CHIM FR II-CH, P285

[3] SYNTHESIS OF PRESQUALENE ALCOHOL [J].

CAMPBELL, RV ;

CROMBIE, L ;

PATTENDE.G .

JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (05) :218-&

[4] SYNTHESIS OF (+ OR -)-PRESQUALENE ALCOHOL, (+ OR -)-PREPHYTOENE ALCOHOL, AND STRUCTURALLY RELATED COMPOUNDS [J].

CAMPBELL, RVM ;

CROMBIE, L ;

FINDLEY, DAR ;

KING, RW ;

PATTENDEN, G ;

WHITING, DA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (10) :897-913

[5] REARRANGEMENT AND FRAGMENTATION REACTIONS IN CARBENOID DECOMPOSITION OF DIAZO HYDROCARBONS [J].

FRIEDMAN, L ;

SHECHTER, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (04) :1002-1003

[6]

Hudlicky T., 1991, COMPREHENSIVE ORGANI, V5, P899, DOI DOI 10.1016/B978-0-08-052349-1.00142-6

[7] NOVEL CONSTRUCTION OF POLYCYCLIC SYSTEMS FUSED TO CYCLOBUTANE BY TANDEM INTRAMOLECULAR MICHAEL-ALDOL REACTION [J].

IHARA, M ;

OHNISHI, M ;

TAKANO, M ;

MAKITA, K ;

TANIGUCHI, N ;

FUKUMOTO, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (11) :4408-4410

[8]

IHARA M, IN PRESS J AM CHEM S

[9] (+)-OVALIFOLIENALONE, A NOVEL SESQUITERPENOID KETONE OF THE ENT-2,3-SECO-ALLOAROMADENDRANE GROUP FROM PLAGIOCHILA-SEMIDECURRENS (LIVERWORT) - X-RAY CRYSTAL AND MOLECULAR-STRUCTURE [J].

MATSUO, A ;

NOZAKI, H ;

ATSUMI, K ;

KATAOKA, H ;

NAKAYAMA, M ;

KUSHI, Y ;

HAYASHI, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (22) :1012-1013

[10] TRIALKYLSILYL TRIFLATES .5. A STEREOSELECTIVE ALDOL-TYPE CONDENSATION OF ENOL SILYL ETHERS AND ACETALS CATALYZED BY TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE [J].

MURATA, S ;

SUZUKI, M ;

NOYORI, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (09) :3248-3249

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