Asymmetric synthesis of a highly functionalized bicyclo[3.2.2]nonene derivative

被引：3

作者：

Tabuchi, Toshiki ^{[1
]}

Urabe, Daisuke ^{[1
]}

Inoue, Masayuki ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1330033, Japan

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 9卷

关键词：

asymmetric synthesis; C-2-symmetry; catalysis; Diels-Alder reaction; Lewis acid; natural product; quaternary carbon; DIELS-ALDER REACTIONS; RING-SYSTEM; RYANODINE; TERPENOIDS;

D O I：

10.3762/bjoc.9.74

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereoselective Diels-Alder reaction between an optically active 1,4-dimethylcycloheptadiene and acrolein was effectively promoted by TBSOTf to produce a bicyclo[3.2.2]nonene derivative bearing two quaternary carbons. Seven additional transformations from the obtained bicycle delivered the C-2-symmetric bicyclo[3.3.2]decene derivative, a key intermediate in our synthetic study of ryanodine.

引用

页码：655 / 663

页数：9

共 29 条

[11] DIELS-ALDER REACTIONS OF CYCLOALKENONES .18. UNUSUAL DIELS-ALDER REACTIONS OF EUCARVONE
GUO, M
MINUTI, L
TATICCHI, A
WENKERT, E
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (04) : 1366 - 1368
[12] A concise route to the C2-symmetric tricyclic skeleton of ryanodine
Hagiwara, Koji
Himuro, Masafumi
Hirama, Masahiro
Inoue, Masayuki
[J]. TETRAHEDRON LETTERS, 2009, 50 (09) : 1035 - 1037
[13] Asymmetric [4+2] cycloadditions employing 1,3-dienes derived from (R)-4-t-butyldimethyl-silyloxy-2-cyclohexen-1-one
Hua, Zhengmao
Chen, Lei
Mei, Yan
Jin, Zhendong
[J]. TETRAHEDRON LETTERS, 2009, 50 (48) : 6621 - 6623
[14] ASYMMETRIC SYNTHESES OF HIGHLY FUNCTIONALIZED BICYCLO[2.2.2]OCTENE DERIVATIVES
Iwatsu, Masafumi
Urabe, Daisuke
Inoue, Masayuki
[J]. HETEROCYCLES, 2010, 82 (01) : 491 - 504
[15] REGIOSPECIFIC PREPARATION OF THERMODYNAMIC SILYL ENOL ETHERS USING BROMOMAGNESIUM DIALKYLAMIDES
KRAFFT, ME
HOLTON, RA
[J]. TETRAHEDRON LETTERS, 1983, 24 (13) : 1345 - 1348
[16] ONE CARBON RING EXPANSIONS OF BRIDGED BICYCLIC KETONES
KROW, GR
[J]. TETRAHEDRON, 1987, 43 (01) : 3 - 38
[17] Lamy-Schelkens D., 1989, TETRAHEDRON LETT, V30, P5891, DOI [10.1016/S0040-4039(01)93498-7, DOI 10.1016/S0040-4039(01)93498-7]
[18] STEREOCHEMICAL VARIATIONS IN THE DIELS-ALDER REACTIONS OF SILOXYDIENES WITH N,N-DIMETHYL ACRYLAMIDE - A REMARKABLE INFLUENCE OF THE LEWIS ACID CATALYST
LAMYSCHELKENS, H
GIOMI, D
GHOSEZ, L
[J]. TETRAHEDRON LETTERS, 1989, 30 (43) : 5887 - 5890
[19] Ryanodine receptor calcium channels and their partners as drug targets
Mackrill, John J.
[J]. BIOCHEMICAL PHARMACOLOGY, 2010, 79 (11) : 1535 - 1543
[20] MARCOS IS, 1994, TETRAHEDRON, V50, P12655

← 1 2 3 →