STEREOSELECTIVE SYNTHESIS OF DELTA(5)-OXONENE AND ITS NOVEL RING CONTRACTION TO DELTA(4)-OXOCENE

被引:28
作者
FUJIWARA, K [1 ]
TSUNASHIMA, M [1 ]
AWAKURA, D [1 ]
MURAI, A [1 ]
机构
[1] HOKKAIDO UNIV, GRAD SCH SCI, DIV CHEM, SAPPORO, HOKKAIDO 060, JAPAN
关键词
D O I
10.1016/0040-4039(95)01773-B
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The stereoselective syntheses of t-3-bromo-r-2, c-9-diethyl- and r-2, c-9-diethyl-t-3-hydroxy-Delta(5)-oxonenes have been achieved by the oxidative acetalization of 2, 9-diethyl-Delta(2,5)-oxonadiene and subsequent reduction. Furthermore, the novel ring contraction of r-2, c-9-dielhyl-t-3-hydroxy-Delta(5)-oxonene to trans-2-(1-bromopropyl)-8-ethyl-Delta(4)-oxocene has been discovered.
引用
收藏
页码:8263 / 8266
页数:4
相关论文
共 30 条
[11]   MARINE NATURAL-PRODUCTS - HALOGENATED ACETYLENIC ETHERS FROM THE SEA HARE APLYSIA-DACTYLOMELA [J].
GOPICHAND, Y ;
SCHMITZ, FJ ;
SHELLY, J ;
RAHMAN, A ;
VANDERHELM, D .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (25) :5192-5197
[12]  
HONMA T, UNPUB
[13]   3 NEW VINYL ACETYLENES FROM THE MARINE RED ALGA LAURENCIA [J].
HOWARD, BM ;
SCHULTE, GR ;
FENICAL, W ;
SOLHEIM, B ;
CLARDY, J .
TETRAHEDRON, 1980, 36 (12) :1747-1751
[14]  
IRIE T, 1965, TETRAHEDRON LETT, P1091
[15]   ENZYMATIC-REACTION OF (3E,6S,7S)-LAUREDIOL AND THE MOLECULAR MODELING STUDIES ON THE CYCLIZATION OF LAUREDIOLS [J].
ISHIHARA, J ;
KANOH, N ;
MURAI, A .
TETRAHEDRON LETTERS, 1995, 36 (05) :737-740
[16]   THE STRUCTURE OF NOTORYNE, A HALOGENATED C15 NONTERPENOID WITH A NOVEL CARBON SKELETON FROM THE RED ALGA LAURENCIA-NIPPONICA YAMADA [J].
KIKUCHI, H ;
SUZUKI, T ;
KUROSAWA, E ;
SUZUKI, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1991, 64 (06) :1763-1775
[17]  
KING TJ, 1979, TETRAHEDRON LETT, P1453
[18]   STEREOSELECTIVE REDUCTION OF BICYCLIC KETALS - A NEW, ENANTIOSELECTIVE SYNTHESIS OF ISOLAUREPINNACIN AND LAUTHISAN SKELETONS [J].
KOTSUKI, H ;
USHIO, Y ;
KADOTA, I ;
OCHI, M .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (21) :5153-5161
[19]   CONSTITUENTS OF MARINE PLANTS .48. ISOLAURALLENE, A NEW NONTERPENOID C-15-LABELED BROMOALLENE, FROM THE RED ALGA LAURENCIA-NIPPONICA YAMADA [J].
KURATA, K ;
FURUSAKI, A ;
SUEHIRO, K ;
KATAYAMA, C ;
SUZUKI, T .
CHEMISTRY LETTERS, 1982, (07) :1031-1034
[20]   REDUCTIVE CLEAVAGES OF CHIRAL ACETALS USING LEWIS ACID-HYDRIDE SYSTEM [J].
MORI, A ;
ISHIHARA, K ;
YAMAMOTO, H .
TETRAHEDRON LETTERS, 1986, 27 (08) :987-990