First stereoselective synthesis of the versatile chiral building block (7aR)-5,6-dihydro-7a-methyl-1H-indene-2,7(4H,7aH)-dione

被引:0
|
作者
Wei, ZL [1 ]
Li, ZY [1 ]
Lin, GQ [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
来源
SYNTHESIS-STUTTGART | 2000年 / 12期
关键词
asymmetric synthesis; microbial reduction; ketols; bicyclic compounds; Wieland-Miescher ketone analog;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A versatile chiral building block (7aR)-5,6-dihydro-7a-methyl-1H-indene-2,7(4H,7aH)-dione (4) was firstly enantiomerically synthesized from the microbial transformation ketol product 6 in 61.3% overall yield and over 96% ee.
引用
收藏
页码:1673 / 1676
页数:4
相关论文
共 50 条
  • [31] (3aR,5R,7S,7aS)-5-[(tert-butyldimethylsilyloxy)-methyl]-7-ethoxy-3-methyl-7,7a-dihydro-3aH-pyrano[4,3-d]isoxazol-4(5H)-one
    Cottier, L
    Srivastava, RM
    Sinou, D
    de Freitas, JR
    Jeanneau, E
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2006, 62 : O540 - O541
  • [32] SYNTHESIS AND STRUCTURAL ASSIGNMENT OF 5,6-DIHYDRO-8-HYDROXY-9-METHOXY-1H,7H-BENZO [IJ] QUINOLIZINE-1,7-DIONE
    WRIGHT, GC
    SCHWAN, TJ
    MILES, NJ
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1974, 11 (06) : 849 - 851
  • [33] (7aR*,12bS*)-8,12b-Dihydro-7aH-indeno[1′,2′:5,6][1,4]selenazino[2,3,4-ij]quinolin-13-ium hydrogen sulfate
    Mammadova, Gunay Z.
    Matsulevich, Zhanna V.
    Borisova, Galina N.
    Borisov, Alexander V.
    Khrustalev, Victor N.
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O3286 - U420
  • [34] 5-Hydroxy-7-phenyl-5-(prop-2-yn-1-yl)-5,6-dihydro-1-benzofuran-2(4H)-one monohydrate
    Torre-Fernandez, Laura
    Suero, Marcos G.
    Garcia-Granda, Santiago
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O2834 - U335
  • [35] The first preparation of enantiopure 1-methyl-7-oxabicyclo[2.2.1]heptan-2-one, a versatile chiral building block for terpenoids
    Guan, YK
    Li, YL
    CHIRALITY, 2005, 17 (02) : 113 - 118
  • [36] THE SYNTHESIS OF (+/-)-IOLIOLIDE OR 6-HYDROXY-5,6,7,7A-TETRAHYDRO-4,4,7A(4H)-TRIMETHYL 2-(6S,7AR)-BENZOFURANNONE BY CYCLIZATION OF HOMOGERANIC ACID
    ZAMARLIK, H
    GNONLONFOUN, N
    ROUESSAC, F
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (11): : 2326 - 2329
  • [37] ANTHRACYCLINES .10. THE ENANTIOSPECIFIC SYNTHESIS OF (-)-(7R)-7-ACETYL-7-HYDROXY-4,4-DIMETHOXY-5,6,7,8-TETRAHYDRONAPHTHALEN-1(4H)-ONE - A TYPE-I CHIRAL DIENONE FOR THE SYNTHESIS OF 7-DEOXYDAUNOMYCINONE
    RUSSELL, RA
    GEE, PS
    IRVINE, RW
    WARRENER, RN
    AUSTRALIAN JOURNAL OF CHEMISTRY, 1984, 37 (08) : 1709 - 1720
  • [38] New synthesis of 5-aryl-5,6-dihydro-7H-[1,2,4]triazolo-[5.1-b][1,3]thiazin-7-ones
    Britsun, VN
    Pirozhenko, VV
    Lozinskii, MO
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2001, 37 (07) : 1056 - 1057
  • [39] Synthesis and transition-metal complexes of novel axially chiral indenes: 4 and 7-(2-methyl-naphthyl)-1h-indene.
    Nguyen, TT
    Sowa, JR
    Liu, C
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U207 - U207
  • [40] THE SYNTHESIS OF 7-CHLORO-5-PENTADEUTERIOPHENYL-1-METHYL-1H-1,5-BENZODIAZEPINE-2,4(3H,5H)DIONE ([2H5]CLOBAZAM)
    BOREL, AG
    ABBOTT, FS
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1990, 28 (07): : 771 - 783