TOTAL SYNTHESIS OF (5R,6S)-DIHETES, (5S,6S)-DIHETES AND (11R,12S)-DIHETES FROM TRICARBONYL ETA-4-BUTADIENYL) IRON(0) COMPLEXES

被引：0
|
作者：
LELLOUCHE, JP [1 ]
GIGOUBARBEDETTE, A [1 ]
GREE, R [1 ]
机构：
[1] ENSCR,SYNTHESES & ACTIVAT BIOMOLEC LAB,CNRS,URA D1 467,F-35700 RENNES,FRANCE
来源：
BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE | 1992年 / 129卷 / 06期
关键词：
TRICARBONYL (ETA-4-BUTADIENYL) IRON COMPLEXES; OSMYLATION; (5,6)-DIHETES; (11,12)-DIHETE; (14,15)-DIDEHYDRO (11,12)-DIHETE;
D O I：
暂无
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
The total synthesis of (5R,6S)-, (5S,6S)- and (11R,12S)-DIHETEs are described starting from the two chiral tricarbonyl (eta4-butadienyl)iron complexes (-)-(2R,5S)-12 and (+)-(2S,5R)-13. This new synthetic approach shows an efficient use of these chiral bifunctionalized iron complexes for the preparation of polyhydroxylated polyenes. The key step of the sequence, ie, the osmylation of a free double bond close to the organonietallic unit, has been studied in detail. The addition Of OsO4 is diastereospecific for the Z-alkenes and highly diastereoselective for the E-alkenes: in both cases, it occurs anti to the Fe(CO)3 group.
引用
收藏
页码：605 / 624
页数：20
相关论文
共 50 条
  • [31] A Stereoselective Synthesis of a Pure (4S,5R,6S)-4-(5,6-Epoxy-6-Phenyl)-gamma$ MIN@Lactone
    Tetrahedron Asymmetry, 6 (1797):
  • [32] ALKYLATION OF (1S,2R,5R,6S,7R)- AND (1R,2R,5R,6S,7S)-5-METHYL-4-OXATRICYCLO-[5.2.1.0/2,6]-8-DECEN-3-ONE - APPLICATION TO THE SYNTHESIS OF (R)-3-ALKYL-5-METHYL-2(5H)-FURANONES
    CORBERA, J
    FONT, J
    MONSALVATJE, M
    ORTUNO, RM
    SANCHEZFERRANDO, F
    JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (18): : 4393 - 4395
  • [33] Bottomonium physics at Υ(4S, 5S, 6S) energies with the Belle detector
    Tamponi, Umberto
    FAIRNESS 2016, 2016, 742
  • [34] Synthesis and herbicidal activity of [3R*,5S*,6S*]-3-benzyloxy-5-methoxy-1,7-dioxaspiro[5.5]undecane and [3R*,5S*,6S*]-3-methoxy-5-benzyloxy-1,7-dioxaspiro[5.5]undecane
    Brimble, MA
    Johnston, AD
    Furneaux, RH
    JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (03): : 471 - 479
  • [35] (1R,3S,5R,6S)-6-Hydroxy-3-tosyloxytropan-8-ium chloride
    Yu, Nian-Xi
    Yang, Li-Min
    Lu, Yang
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O317 - U2036
  • [36] Synthesis of (-)-(5R,6S)-6-acetoxyhexadecanolide, a mosquito oviposition attractant pheromone of Culex pipiens fatigans
    Sabitha, Gowravaram
    Swapna, R.
    Reddy, E. Venkata
    Yadav, J. S.
    SYNTHESIS-STUTTGART, 2006, (24): : 4242 - 4246
  • [37] STRUCTURE OF PIVALOYLOXYMETHYL (3S,5R,6S)-6-BROMOPENICILLANATE 1,1-DIOXIDE
    ALZARI, PM
    RONCO, AE
    RIVERO, BE
    PUNTE, G
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1986, 42 : 1032 - 1034
  • [38] A NOVEL AND STEREOSPECIFIC SYNTHESIS OF (5R,6S)-6-(AMINOMETHYL)-2-(ETHYLTHIO)PENEMCARBOXYLIC ACID
    WELCH, WM
    GUARINO, KJC
    JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (19): : 4401 - 4403
  • [39] SYNTHESIS AND ACID-CATALYZED REARRANGEMENT OF (1R,2R,5S,6S)-TRICYCLO[4.3.1.12,5]UNDECANE
    TAKAISHI, N
    INAMOTO, Y
    AIGAMI, K
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (09): : 789 - 792
  • [40] (5R, 6S)-6-methyl-5-(phenylsulfonylacetyl)-bicyclo[2.2.1] hept-2-ene
    Pei, Wen
    Wang, Yongjiang
    Sun, Mengzhan
    Xiong, Xiaobo
    Yu, Changquan
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2007, 63 : O2142 - O2143
12345