(ETA-6-ARENE)CHROMIUM COMPLEXES IN ORGANIC-SYNTHESIS - SYNTHESIS OF (+/-)-DIHYDROXYSERRULATIC ACID

被引:43
作者
UEMURA, M
NISHIMURA, H
MINAMI, T
HAYASHI, Y
机构
[1] Osaka City University, Osaka 558, Sugimoto 3-3-138, Sumiyoshi-ku
[2] Sagami Chemical Research Center, Sagamihara, Kanagawa 299
关键词
D O I
10.1021/ja00014a036
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The title compound 1 has been synthesized by utilizing some characteristic properties of (eta-6-arene)chromium complexes. The synthesis of dihydroxyserrulatic acid (1) consists of the following three key steps: (1) nucleophilic addition of a dithianyl group at the meta position to an electron-donating methoxy group, (2) trans arrangement of two benzylic substituents (at C-1 and C-4 positions), and (3) stereocontrol between C-4 and C-11 positions (extracyclic position). These three steps have been realized with high regio- and stereoselectivities by utilizing (arene)chromium complexes.
引用
收藏
页码:5402 / 5410
页数:9
相关论文
共 69 条
[1]   CONFORMATIONAL EFFECTS OF NUCLEOPHILIC AND ELECTROPHILIC ATTACK ON (ARENE)CHROMIUM TRICARBONYL COMPLEXES [J].
ALBRIGHT, TA ;
CARPENTER, BK .
INORGANIC CHEMISTRY, 1980, 19 (10) :3092-3097
[2]   SYNTHETIC APPLICATIONS OF LITHIATED TRICARBONYL-ETA-6-ARENECHROMIUM(O) COMPLEXES - COPPER AND PALLADIUM CATALYZED SUBSTITUTIONS [J].
BESWICK, PJ ;
LEACH, SJ ;
MASTERS, NF ;
WIDDOWSON, DA .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (01) :46-48
[3]   STEREOSELECTIVE ALDOL REACTIONS WITH ALPHA-UNSUBSTITUTED CHIRAL ENOLATES [J].
BRAUN, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (01) :24-37
[4]   DIASTEREOSPECIFIC (2,3) - WITTIG-REARRANGEMENT IN CHROME TRICARBONYL ALLYL ETHERS [J].
BROCARD, J ;
MAHMOUDI, M ;
PELINSKI, L ;
MACIEJEWSKI, L .
TETRAHEDRON LETTERS, 1989, 30 (19) :2549-2552
[5]   TOTAL SYNTHESIS OF (-)-PSEUDOPTEROSIN-A [J].
BROKA, CA ;
CHAN, S ;
PETERSON, B .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (07) :1584-1586
[6]   THE CHEMISTRY OF EREMOPHILA SPP .17. (1R,4S)-CALAMENENE - CHEMICAL CORRELATION WITH THE DITERPENE ANALOGS OF EREMOPHILA [J].
BUNKO, JD ;
GHISALBERTI, EL ;
JEFFERIES, PR .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1981, 34 (10) :2237-2242
[7]   (-)-7-HYDROXYCALAMENENE, A PHYTOALEXIN FROM TILIA-EUROPEA [J].
BURDEN, RS ;
KEMP, MS .
PHYTOCHEMISTRY, 1983, 22 (04) :1039-1040
[8]  
BUSE CT, 1978, TETRAHEDRON LETT, P1685
[9]  
CARTER OL, 1966, J CHEM SOC A, P288
[10]   TRANSITION-METAL MEDIATED ORGANIC-SYNTHESIS - THE SYNTHESIS OF MORACIN-M [J].
CLOUGH, JM ;
MANN, IS ;
WIDDOWSON, DA .
TETRAHEDRON LETTERS, 1987, 28 (23) :2645-2648