BETA-LACTAMS .3. ASYMMETRIC TOTAL SYNTHESIS OF NEW NONNATURAL 1-BETA-METHYLCARBAPENEMS EXHIBITING STRONG ANTIMICROBIAL ACTIVITIES AND STABILITY AGAINST HUMAN RENAL DEHYDROPEPTIDASE-I

被引：72

作者：

NAGAO, Y ^{[1
]}

NAGASE, Y ^{[1
]}

KUMAGAI, T ^{[1
]}

MATSUNAGA, H ^{[1
]}

ABE, T ^{[1
]}

SHIMADA, O ^{[1
]}

HAYASHI, T ^{[1
]}

INOUE, Y ^{[1
]}

机构：

[1] LEDERLE JAPAN LTD,CHEM & FORMULAT LABS,SHIKI,SAITAMA 353,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 15期

关键词：

D O I：

10.1021/jo00041a033

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric synthesis of 11, the precursor to chiral (3R,4R)-3-[(1R)-1-[(tert-butyldimethylsilyl)oxy]ethyl]-4-acetoxyazetidin-2-one (3) was achieved by utilizing a highly diastereoselective aldol-type reaction of acetaldehyde and the chiral tin(II) enolate of 5. Similar diastereoselective alkylations of chiral and achiral tin(II) enolates 13a-d with chiral 3 were also performed to obtain the desired alkylated azetidin-2-ones (17a-d). Compounds 17a,b were successfully converted to new, non-natural 1-beta-methylcarbapenems 1a and 1b, which exhibited strong and wide-ranging antimicrobial activities and excellent stability against human renal dehydropeptidase-I.

引用

页码：4243 / 4249

页数：7

共 24 条

[1] SIMPLE AND HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF A 1-BETA-METHYLCARBAPENEM KEY INTERMEDIATE INVOLVING DIVALENT TIN ENOLATES
DEZIEL, R
FAVREAU, D
[J]. TETRAHEDRON LETTERS, 1986, 27 (47) : 5687 - 5690
[2] EVANS DA, 1986, TETRAHEDRON LETT, V31, P4961
[3] LEWIS ACID MEDIATED CONDENSATION OF CHIRAL IMIDE ENOLATES - A GENERAL-APPROACH TO THE SYNTHESIS OF CHIRAL CARBAPENEM PRECURSORS
FUENTES, LM
SHINKAI, I
SALZMANN, TN
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (15) : 4675 - 4676
[4] ACYCLIC STEREOSELECTION .7. STEREOSELECTIVE SYNTHESIS OF 2-ALKYL-3-HYDROXY CARBONYL-COMPOUNDS BY ALDOL CONDENSATION
HEATHCOCK, CH
BUSE, CT
KLESCHICK, WA
PIRRUNG, MC
SOHN, JE
LAMPE, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (06) : 1066 - 1081
[5] HIKIDA M, UNPUB ANTIMICROB AGE
[6] HIKIDA M, 1988, 28TH INT C ANT AG CH
[7] SIMPLE, STEREOCONTROLLED SYNTHESIS OF 1-BETA-METHYLCARBAPENEM ANTIBIOTICS FROM 3(R)-HYDROXYBUTYRIC ACID
IIMORI, T
SHIBASAKI, M
[J]. TETRAHEDRON LETTERS, 1986, 27 (19) : 2149 - 2152
[8] HIGHLY ENANTIOSELECTIVE ALDOL-TYPE REACTION OF 3-ACETYLTHIAZOLIDINE-2-THIONE WITH ACHIRAL ALDEHYDES
IWASAWA, N
MUKAIYAMA, T
[J]. CHEMISTRY LETTERS, 1983, (03) : 297 - 298
[9] A NOVEL AND EFFICIENT SYNTHESIS OF THE KEY INTERMEDIATE OF 1-BETA-METHYLCARBAPENEM ANTIBIOTICS FROM (S)-METHYL 3-HYDROXY-2-METHYLPROPIONATE
KAWABATA, T
KIMURA, Y
ITO, Y
TERASHIMA, S
SASAKI, A
SUNAGAWA, M
[J]. TETRAHEDRON LETTERS, 1986, 27 (51) : 6241 - 6244
[10] OXIDATIVE N-DEARYLATION OF 2-AZETIDINONES - PARA-ANISIDINE AS A SOURCE OF AZETIDINONE NITROGEN
KRONENTHAL, DR
HAN, CY
TAYLOR, MK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (14) : 2765 - 2768

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