DIASTEREOSELECTIVE IODOCARBOCYCLIZATION OF 4-PENTENYLMALONATE DERIVATIVES - APPLICATION TO CYCLOSARKOMYCIN SYNTHESIS

被引:30
作者
KITAGAWA, O [1 ]
INOUE, T [1 ]
TAGUCHI, T [1 ]
机构
[1] TOKYO COLL PHARM,HACHIOJI,TOKYO 19203,JAPAN
关键词
D O I
10.1016/S0040-4039(00)79965-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The iodocarbocyclization of 4-pentenylmalonate I having a substituent at the 2 or 3 position effectively proceeded by treating I with I-2 and Ti(OtBu)(4) in the presence of CuO. Stereoelectronic effect of the subtituent at allylic position on diastereoselectivity was notable. As an application of the present reaction, the efficient synthesis of cyclosarkomycin 7 was achieved.
引用
收藏
页码:1059 / 1062
页数:4
相关论文
共 17 条
[1]   ELECTROPHILIC LACTONIZATION AS A TOOL IN ACYCLIC STEREOCONTROL - SYNTHESIS OF SERRICORNIN [J].
BARTLETT, PA ;
RICHARDSON, DP ;
MYERSON, J .
TETRAHEDRON, 1984, 40 (12) :2317-2327
[2]   THE IODINATION AND IODOCYCLISATION OF SOME ALKENYLMALONATES [J].
BECKWITH, ALJ ;
TOZER, MJ .
TETRAHEDRON LETTERS, 1992, 33 (34) :4975-4978
[3]   STEREOCONTROLLED CYCLOFUNCTIONALIZATIONS OF DOUBLE-BONDS THROUGH HETEROCYCLIC INTERMEDIATES [J].
CARDILLO, G ;
ORENA, M .
TETRAHEDRON, 1990, 46 (10) :3321-3408
[4]   MODELING CHEMICAL-REACTIVITY .7. THE EFFECT OF A CHANGE IN RATE-LIMITING STEP ON THE STEREOSELECTIVITY OF ELECTROPHILIC ADDITION TO ALLYLIC ALCOHOLS AND RELATED CHIRAL ALKENES [J].
CHAMBERLIN, AR ;
MULHOLLAND, RL ;
KAHN, SD ;
HEHRE, WJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (03) :672-677
[5]   IODOCYCLIZATION OF ALLYLIC ALCOHOL DERIVATIVES CONTAINING INTERNAL NUCLEOPHILES - CONTROL OF STEREOSELECTIVITY BY SUBSTITUENTS IN THE ACYCLIC PRECURSORS [J].
CHAMBERLIN, AR ;
DEZUBE, M ;
DUSSAULT, P ;
MCMILLS, MC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (18) :5819-5825
[6]   A ONE-STEP SYNTHESIS OF FUNCTIONALIZED LACTAMS AND SPIROLACTAMS FROM UNSATURATED BETA-KETOAMIDES [J].
COSSY, J ;
THELLEND, A .
TETRAHEDRON LETTERS, 1990, 31 (10) :1427-1428
[7]   ATOM TRANSFER CYCLIZATION REACTIONS OF ALPHA-IODO ESTERS, KETONES, AND MALONATES - EXAMPLES OF SELECTIVE 5-EXO, 6-ENDO, 6-EXO, AND 7-ENDO RING CLOSURES [J].
CURRAN, DP ;
CHANG, CT .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (13) :3140-3157
[8]   CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION [J].
GAO, Y ;
HANSON, RM ;
KLUNDER, JM ;
KO, SY ;
MASAMUNE, H ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) :5765-5780
[9]  
GUNTHER HJ, 1984, LIEBIGS ANN CHEM, P15
[10]   ENANTIOSELECTIVE HALOCYCLIZATION REACTION USING A CHIRAL TITANIUM COMPLEX [J].
KITAGAWA, O ;
HANANO, T ;
TANABE, K ;
SHIRO, M ;
TAGUCHI, T .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (14) :1005-1007