Synthesis of carbocycles via intramolecular conjugate additions: Another solution to the terpenoid side chain stereochemistry problem

被引:21
作者
Guevel, AC [1 ]
Hart, DJ [1 ]
机构
[1] OHIO STATE UNIV,DEPT CHEM,COLUMBUS,OH 43210
关键词
D O I
10.1021/jo951531m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Intramolecular conjugate additions of keto esters 7-11, mediated by pyrrolidine-acetic acid, provide perhydroindans or bicyclo[6.3.0]undecanes with high levels of diastereoselectivity at the acyclic stereogenic center. Levels of acyclic diastereoselection depend on starting unsaturated ester olefin geometry.
引用
收藏
页码:465 / 472
页数:8
相关论文
共 55 条
[1]   SELECTIVE GAMMA-SUBSTITUTION OF ALPHA,BETA-UNSATURATED ESTERS VIA ALPHA-TRIMETHYLSILYL BETA,GAMMA-UNSATURATED ESTERS [J].
ALBAUGHROBERTSON, P ;
KATZENELLENBOGEN, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (26) :5288-5302
[2]   STEREOSELECTIVITY OF INTRAMOLECULAR NITRILE OXIDE CYCLOADDITIONS TO Z-CHIRAL ALKENE AND E-CHIRAL ALKENE [J].
ANNUNZIATA, R ;
CINQUINI, M ;
COZZI, F ;
GENNARI, C ;
RAIMONDI, L .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (21) :4674-4681
[3]  
BIERNACKI W, 1979, SYNTHESIS-STUTTGART, P37
[4]   ASYMMETRIC MICHAEL-ADDITIONS - PRACTICALLY COMPLETELY DIASTEREOSELECTIVE AND ENANTIOSELECTIVE ALKYLATIONS OF THE ENAMINE FROM CYCLOHEXANONE AND PROLINYL METHYL-ETHER BY OMEGA-NITROSTYRENES TO GIVE U- 2-(1'-ARYL-2'-NITROETHYL)CYCLOHEXANONES [J].
BLARER, SJ ;
SCHWEIZER, WB ;
SEEBACH, D .
HELVETICA CHIMICA ACTA, 1982, 65 (05) :1637-1654
[5]   SYNTHETIC APPROACH TO DENDROBINE SKELETON [J].
BRATTESANI, DN ;
HEATHCOCK, CH .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (15) :2165-2170
[6]  
BROOKERMILBURN KL, 1993, SYNLETT, P592
[7]   ALKENE SYNTHESIS VIA BETA-FUNCTIONALIZED ORGANOSILICON COMPOUNDS [J].
CHAN, TH .
ACCOUNTS OF CHEMICAL RESEARCH, 1977, 10 (12) :442-448
[8]   SYNTHETIC APPROACHES TO THE AXANE FAMILY OF SESQUITERPENOIDS - TOTAL SYNTHESIS OF DL-AXAMIDE-4, DL-AXISONITRILE-4, AND DL-AXISOTHIOCYANATE-4 [J].
CHENERA, B ;
CHUANG, CP ;
HART, DJ ;
LAI, CS .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) :2018-2029
[9]   EVIDENCE FOR A REVERSIBLE D,PI-STAR-COMPLEXATION, BETA-CUPRATION SEQUENCE IN THE CONJUGATE ADDITION-REACTION OF GILMAN REAGENTS WITH ALPHA-ENONES, BETA-ENONES [J].
COREY, EJ ;
BOAZ, NW .
TETRAHEDRON LETTERS, 1985, 26 (49) :6015-6018
[10]   THE ASYMMETRIC MICHAEL ADDITION PROCESS INVOLVING CHIRAL IMINES - STEREOCHEMICAL DATA IN SUPPORT OF A CYCLIC-LIKE TRANSITION-STATE [J].
DANGELO, J ;
GUINGANT, A ;
RICHE, C ;
CHIARONI, A .
TETRAHEDRON LETTERS, 1988, 29 (22) :2667-2670