Efficient, Enantioselective Assembly of Silanediol Protease Inhibitors

被引：36

作者：

Bo, Yingjian ^{[1
]}

Singh, Swapnil ^{[1
]}

Hoan Quoc Duong ^{[1
]}

Cao, Cui ^{[1
]}

Sieburth, Scott McN ^{[1
]}

机构：

[1] Temple Univ, Dept Chem, Philadelphia, PA 19122 USA

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 07期

基金：

美国国家卫生研究院;

关键词：

ASYMMETRIC CATALYSIS; PRINCIPLES; CHEMISTRY; ALCOHOLS; CARBONYL; DESIGN;

D O I：

10.1021/ol2002978

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A five-step assembly of silicon-protected dipeptide mimics from commercially available reagents is described. This methodology makes silanediol protease inhibitors readily available for the first time. The sequence features asymmetric hydrosilylation, a novel reduction of a silyl ether to a silyllithium reagent, and addition of this dianion to a sulfinimine, to produce the complete inhibitor skeleton with full control of stereochemistry. Oxidation of the primary alcohol to an acid completes the synthesis.

引用

页码：1787 / 1789

页数：3

共 32 条

[1] Molecular recognition of protein-ligand complexes: Applications to drug design
Babine, RE
Bender, SL
[J]. CHEMICAL REVIEWS, 1997, 97 (05) : 1359 - 1472
[2] THE FORMATION OF ARYLSILYLPOTASSIUM COMPOUNDS
BENKESER, RA
LANDESMAN, H
FOSTER, DJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (03) : 648 - 650
[3] Berens U, 2000, ANGEW CHEM INT EDIT, V39, P1981, DOI 10.1002/1521-3773(20000602)39:11<1981::AID-ANIE1981>3.0.CO
[4] 2-3
[5] ASYMMETRIC CATALYSIS - MECHANISM OF ASYMMETRIC CATALYTIC INTRAMOLECULAR HYDROSILATION
BERGENS, SH
NOHEDA, P
WHELAN, J
BOSNICH, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (06) : 2128 - 2135
[6] ASYMMETRIC CATALYSIS - PRODUCTION OF CHIRAL DIOLS BY ENANTIOSELECTIVE CATALYTIC INTRAMOLECULAR HYDROSILATION OF OLEFINS
BERGENS, SH
NOHEDA, P
WHELAN, J
BOSNICH, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (06) : 2121 - 2128
[7] An enantioselective synthesis of (S)-(+)-3-aminomethyl-5-methylhexanoic acid via asymmetric hydrogenation
Burk, MJ
de Koning, PD
Grote, TM
Hoekstra, MS
Hoge, G
Jennings, RA
Kissel, WS
Le, TV
Lennon, IC
Mulhern, TA
Ramsden, JA
Wade, RA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (14) : 5731 - 5734
[8] Drug design with a new transition state analog of the hydrated carbonyl: silicon-based inhibitors of the HIV protease
Chen, CA
Sieburth, SM
Glekas, A
Hewitt, GW
Trainor, GL
Erickson-Viitanen, S
Garber, SS
Cordova, B
Jeffry, S
Klabe, RM
[J]. CHEMISTRY & BIOLOGY, 2001, 8 (12): : 1161 - 1166
[9] Alzheimer's disease: strategies for disease modification
Citron, Martin
[J]. NATURE REVIEWS DRUG DISCOVERY, 2010, 9 (05) : 387 - 398
[10] A versatile and highly selective hypervalent iodine (III)/2,2,6,6-tetramethyl-1-piperidinyloxyl-mediated oxidation of alcohols to carbonyl compounds
DeMico, A
Margarita, R
Parlanti, L
Vescovi, A
Piancatelli, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (20) : 6974 - 6977

← 1 2 3 4 →