SYNTHESIS OF ALPHA-HYDROXY STATINE THROUGH A FACIALLY SELECTIVE OSMYLATION OF A CHIRAL ALPHA-AMIDO CROTONATE

被引：10

作者：

DEE, MF ^{[1
]}

ROSATI, RL ^{[1
]}

机构：

[1] PFIZER INC,DIV CENT RES,GROTON,CT 06340

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1995年 / 5卷 / 09期

关键词：

D O I：

10.1016/0960-894X(95)00150-R

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

alpha-hydroxy statine 5 was synthesized by osmylation of amido crotonate 6 and incorporated into peptide framework 9, resulting in an active renin inhibitor; predicted stereochemical preferences for renin inhibition were confirmed by x-ray analysis and biochemical determinations. The facial selectivity of the osmylation is consistent with the Vedejs model.

引用

页码：949 / 952

页数：4

共 18 条

[1] NOVEL RENIN INHIBITORS - SYNTHESIS OF AMINOSTATINE AND COMPARISON WITH STATINE-CONTAINING ANALOGS
ARROWSMITH, RJ
CARTER, K
DANN, JG
DAVIES, DE
HARRIS, CJ
MORTON, JA
LISTER, P
ROBINSON, JA
WILLIAMS, DJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (10) : 755 - 757
[2] BINDRA JS, 1989, Patent No. 4749687
[3] NOVEL RENIN INHIBITORS CONTAINING THE AMINO-ACID STATINE
BOGER, J
LOHR, NS
ULM, EH
POE, M
BLAINE, EH
FANELLI, GM
LIN, TY
PAYNE, LS
SCHORN, TW
LAMONT, BI
VASSIL, TC
STABILITO, II
VEBER, DF
RICH, DH
BOPARI, AS
[J]. NATURE, 1983, 303 (5912) : 81 - 84
[4] ON STEREOCHEMISTRY OF OSMIUM TETRAOXIDE OXIDATION OF ALLYLIC ALCOHOL SYSTEMS - EMPIRICAL RULE
CHA, JK
CHRIST, WJ
KISHI, Y
[J]. TETRAHEDRON, 1984, 40 (12) : 2247 - 2255
[5] ENANTIOSELECTIVE VICINAL HYDROXYLATION OF TERMINAL AND E-1,2-DISUBSTITUTED OLEFINS BY A CHIRAL COMPLEX OF OSMIUM TETRAOXIDE - AN EFFECTIVE CONTROLLER SYSTEM AND A RATIONAL MECHANISTIC MODEL
COREY, EJ
JARDINE, PD
VIRGIL, S
YUEN, PW
CONNELL, RD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (26) : 9243 - 9244
[6] STEREOSPECIFIC SYNTHESIS OF A NEW MORPHINE PARTIAL STRUCTURE
HAEFLIGER, W
KLOPPNER, E
[J]. HELVETICA CHIMICA ACTA, 1982, 65 (06) : 1837 - 1852
[7] A BRIEF TOTAL SYNTHESIS OF N-BENZOYL-D,L-DAUNOSAMINE
HAUSER, FM
RHEE, RP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (01) : 227 - 228
[8] STEREOSELECTIVE NITRILE OXIDE CYCLO-ADDITIONS TO CHIRAL ALLYL ETHERS AND ALCOHOLS - THE INSIDE ALKOXY EFFECT
HOUK, KN
MOSES, SR
WU, YD
RONDAN, NG
JAGER, V
SCHOHE, R
FRONCZEK, FR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (13) : 3880 - 3882
[9] NEW HUMAN RENIN INHIBITORS CONTAINING AN UNNATURAL AMINO-ACID, NORSTATINE
IIZUKA, K
KAMIJO, T
KUBOTA, T
AKAHANE, K
UMEYAMA, H
KISO, Y
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (04) : 701 - 704
[10] DIASTEREOSELECTIVITY IN THE OSMIUM-CATALYZED DIHYDROXYLATION OF ALLYLIC AMIDES AND CARBAMATES
KRYSAN, DJ
ROCKWAY, TW
HAIGHT, AR
[J]. TETRAHEDRON-ASYMMETRY, 1994, 5 (04) : 625 - 632

← 1 2 →