Improved procedure for Julia-Colonna asymmetric epoxidation of α,β-unsaturated ketones:: total synthesis of diltiazem and Taxol™ side-chain

被引：140
作者：
Adger, BM
Barkley, JV
Bergeron, S
Cappi, MW
Flowerdew, BE
Jackson, MP
McCague, R
Nugent, TC
Roberts, SM [1 ]
机构：
[1] Univ Liverpool, Robert Robinson Labs, Dept Chem, Liverpool L69 3BX, Merseyside, England
[2] Chirosci Ltd, Cambridge CB4 4WE, England
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 23期
关键词：
D O I：
10.1039/a704413e
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Poly-L-leucine catalyses the asymmetric epoxidation of enones 1-6 efficiently in a non-aqueous medium to provide the epoxy ketones 7-12 (70-91% yield; 80 to greater than or equal to 95% ee). The strategy was used to make diltiazem 16 and the Taxol(TM) Side chain 23 in single enantiomer form.
引用
收藏
页码：3501 / 3507
页数：7
相关论文
共 31 条
  • [1] AN EFFICIENT ASYMMETRIC-SYNTHESIS OF SUBSTITUTED PHENYL GLYCIDIC ESTERS
    BAURES, PW
    EGGLESTON, DS
    FLISAK, JR
    GOMBATZ, K
    LANTOS, I
    MENDELSON, W
    REMICH, JJ
    [J]. TETRAHEDRON LETTERS, 1990, 31 (45) : 6501 - 6504
  • [2] A SIMPLE AND HIGHLY DIASTEREOSELECTIVE PREPARATION OF GLYCAL EPOXIDES USING THE MCPBA-KF COMPLEX
    BELLUCCI, G
    CATELANI, G
    CHIAPPE, C
    DANDREA, F
    [J]. TETRAHEDRON LETTERS, 1994, 35 (45) : 8433 - 8436
  • [3] Asymmetric epoxidation of enones employing polymeric alpha-amino acids in non-aqueous media
    Bentley, PA
    Bergeron, S
    Cappi, MW
    Hibbs, DE
    Hursthouse, MB
    Nugent, TC
    Pulido, R
    Roberts, SM
    Wu, LE
    [J]. CHEMICAL COMMUNICATIONS, 1997, (08) : 739 - 740
  • [4] Catalytic asymmetric epoxidation of alpha,beta-unsaturated ketones promoted by lanthanoid complexes
    Bougauchi, M
    Watanabe, S
    Arai, T
    Sasai, H
    Shibasaki, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (09) : 2329 - 2330
  • [5] OXIDATION REACTIONS USING UREA HYDROGEN-PEROXIDE - A SAFE ALTERNATIVE TO ANHYDROUS HYDROGEN-PEROXIDE
    COOPER, MS
    HEANEY, H
    NEWBOLD, AJ
    SANDERSON, WR
    [J]. SYNLETT, 1990, (09) : 533 - 535
  • [6] Cromer D. T., 1974, INT TABLES XRAY CRYS, V4
  • [7] A PRACTICAL, HIGHLY ENANTIOSELECTIVE SYNTHESIS OF THE TAXOL SIDE-CHAIN VIA ASYMMETRIC CATALYSIS
    DENG, L
    JACOBSEN, EN
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (15) : 4320 - 4323
  • [8] TAXOTERE(R) BY ESTERIFICATION WITH STEREOCHEMICALLY WRONG (2S,3S)-PHENYLISOSERINE DERIVATIVES
    DENIS, JN
    KANAZAWA, AM
    GREENE, AE
    [J]. TETRAHEDRON LETTERS, 1994, 35 (01) : 105 - 108
  • [9] AN IMPROVED SYNTHESIS OF THE TAXOL SIDE-CHAIN AND OF RP-56976
    DENIS, JN
    CORREA, A
    GREENE, AE
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) : 1957 - 1959
  • [10] Remarkable chemo-, regio-, and enantioselectivity in lipase-catalyzed hydrolysis: Efficient resolution of (+/-)-threo-ethyl 3-(4-methoxyphenyl)-2,3-diacetoxypropionate leading to chiral intermediates of (+)-diltiazem
    Desai, SB
    Argade, NP
    Ganesh, KN
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (19) : 6730 - 6732
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