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

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 45期

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

页码：8263 / 8266

页数：4

共 30 条

[11] MARINE NATURAL-PRODUCTS - HALOGENATED ACETYLENIC ETHERS FROM THE SEA HARE APLYSIA-DACTYLOMELA
GOPICHAND, Y
SCHMITZ, FJ
SHELLY, J
RAHMAN, A
VANDERHELM, D
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (25) : 5192 - 5197
[12] HONMA T, UNPUB
[13] 3 NEW VINYL ACETYLENES FROM THE MARINE RED ALGA LAURENCIA
HOWARD, BM
SCHULTE, GR
FENICAL, W
SOLHEIM, B
CLARDY, J
[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
ISHIHARA, J
KANOH, N
MURAI, A
[J]. 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
KIKUCHI, H
SUZUKI, T
KUROSAWA, E
SUZUKI, M
[J]. 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
KOTSUKI, H
USHIO, Y
KADOTA, I
OCHI, M
[J]. 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
KURATA, K
FURUSAKI, A
SUEHIRO, K
KATAYAMA, C
SUZUKI, T
[J]. CHEMISTRY LETTERS, 1982, (07) : 1031 - 1034
[20] REDUCTIVE CLEAVAGES OF CHIRAL ACETALS USING LEWIS ACID-HYDRIDE SYSTEM
MORI, A
ISHIHARA, K
YAMAMOTO, H
[J]. TETRAHEDRON LETTERS, 1986, 27 (08) : 987 - 990

← 1 2 3 →