1-BETA-METHYLTHIENAMYCIN - SOME STEREOCONTROLLED APPROACHES TOWARDS THE KEY INTERMEDIATE

被引：13

作者：

GURJAR, MK

BHANU, MN

KHARE, VB

BHANDARI, A

DESHMUKH, MN

RAO, AVR

机构：

[1] Indian Institute of Chemical Technology, Hyderabad

来源：

TETRAHEDRON | 1991年 / 47卷 / 34期

关键词：

1-BETA-METHYLTHIENAMYCIN; CARBAPENEM ANTIBIOTICS; STEREOSPECIFIC HYDROGENATION; STEREOSELECTIVE HYDROBORATION; ALLYLIC HYDROXYLATION;

D O I：

10.1016/S0040-4020(01)96165-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two stereocontrolled approaches towards a precursor of 1 beta-methyl-thienamycin, have been accomplished by involving stereospecific hydrogenation of 13 and stereoselective hydroboration oxidation of 9. The latter compounds were obtained from the easily accessible chiral building block 7. The hydroboration-oxidation approach was extended to 18 in which the optically active 1R- (1-hydroxy ethyl) side-chain was incorporated. The highly stereoselective hydroboration-oxidation reaction of 9 is explained by considering Houk's models.

引用

页码：7117 / 7128

页数：12

共 41 条

[1] STRUCTURE AND ABSOLUTE-CONFIGURATION OF THIENAMYCIN
ALBERSSCHONBERG, G
ARISON, BH
HENSENS, OD
HIRSHFIELD, J
HOOGSTEEN, K
KACZKA, EA
RHODES, RE
KAHAN, JS
KAHAN, FM
RATCLIFFE, RW
WALTON, E
RUSWINKLE, LJ
MORIN, RB
CHRISTENSEN, BG
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (20) : 6491 - 6499
[2] THIENAMYCIN TOTAL SYNTHESIS - STEREOCONTROLLED INTRODUCTION OF THE HYDROXYETHYL SIDE-CHAIN
BOUFFARD, FA
CHRISTENSEN, BG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (11) : 2208 - 2212
[3] Brown A. G., 1984, RECENT ADV CHEM BETA
[4] DIASTEREOCONTROL IN RHODIUM-CATALYZED HYDROBORATION OF CHIRAL ACYCLIC ALLYLIC ALCOHOL DERIVATIVES
BURGESS, K
OHLMEYER, MJ
[J]. TETRAHEDRON LETTERS, 1989, 30 (04) : 395 - 398
[5] MANIPULATION OF SUBSTRATE-CONTROLLED DIASTEREOSELECTIVITIES IN HYDROBORATIONS IN ACYCLIC ALLYLAMINE DERIVATIVES
BURGESS, K
OHLMEYER, MJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (03) : 1027 - 1036
[6] CHRISTENSEN BG, 1989, CHEM BRIT, P371
[7] RECENT DEVELOPMENTS IN THE FIELD OF BETA-LACTAM ANTIBIOTICS
DURCKHEIMER, W
BLUMBACH, J
LATTRELL, R
SCHEUNEMANN, KH
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (03): : 180 - 202
[8] RHODIUM(I)-CATALYZED HYDROBORATION OF OLEFINS - THE DOCUMENTATION OF REGIOCHEMICAL AND STEREOCHEMICAL CONTROL IN CYCLIC AND ACYCLIC SYSTEMS
EVANS, DA
FU, GC
HOVEYDA, AH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (20) : 6917 - 6918
[9] A STEREOCONTROLLED SYNTHESIS OF AN IMPORTANT INTERMEDIATE FOR THE PREPARATION OF 1-BETA-METHYLCARBAPENEM ANTIBIOTICS
FUENTES, LM
SHINKAI, I
KING, A
PURICK, R
REAMER, RA
SCHMITT, SM
CAMA, L
CHRISTENSEN, BG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (12) : 2563 - 2567
[10] FUKUMOTO K, 1989, JCS P1, P2215

← 1 2 3 4 5 →