Diastereoselective addition of chlorotitanium enolates of N-acyl thiazolidinethione to activated imines — A novel synthesis of β-lactams

Marike Herold-Dublin; Dennis C Liotta

doi:10.1139/v06-179

Diastereoselective addition of chlorotitanium enolates of N-acyl thiazolidinethione to activated imines — A novel synthesis of β-lactams

Canadian Journal of Chemistry ◽

10.1139/v06-179 ◽

2006 ◽

Vol 84 (12) ◽

pp. 1696-1699 ◽

Cited By ~ 3

Author(s):

Marike Herold-Dublin ◽

Dennis C Liotta

Keyword(s):

Key Words ◽

Lewis Acids ◽

Cholesterol Absorption ◽

Efficient Synthesis ◽

Enantiomerically Pure ◽

Novel Synthesis ◽

Cholesterol Absorption Inhibitor ◽

Diastereoselective Addition

We report a novel methodology for preparing enantiomerically pure β-lactams, starting from nitriles in diastereomeric ratios up to 10:1. The power of the methodology was demonstrated by the efficient synthesis of the cholesterol absorption inhibitor SCH 48462.Key words: β-lactam, N-metalloaldimine, titanium Lewis acids, cholesterol absorption inhibitor.

Treatment with a Cholesterol Absorption Inhibitor (FM-VP4) Reduces Body Mass and Adipose Accumulation in Developing and Pre-Obese Mice

Drug Development and Industrial Pharmacy ◽

10.1080/03639040601133746 ◽

2007 ◽

Vol 33 (10) ◽

pp. 1058-1069 ◽

Cited By ~ 8

Author(s):

Sheila J. Thornton ◽

Corinna Warburton ◽

Kishor M. Wasan ◽

Piotr Kozlowski

Keyword(s):

Body Mass ◽

Cholesterol Absorption ◽

Obese Mice ◽

Cholesterol Absorption Inhibitor

The potent cholesterol absorption inhibitor, ezetimibe, ablates hypercholesterolemia and hypertriglyceridemia in a model of combined hyperlipidemia

Atherosclerosis ◽

10.1016/s0021-9150(00)80599-7 ◽

2000 ◽

Vol 151 (1) ◽

pp. 132 ◽

Cited By ~ 1

Author(s):

M. van Heek ◽

T. Austin ◽

J. Cook ◽

C. Farley ◽

G. Tetzloff ◽

...

Keyword(s):

Cholesterol Absorption ◽

Cholesterol Absorption Inhibitor

A gold-catalyzed alkyne-diol cycloisomerization for the synthesis of oxygenated 5,5-spiroketals

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.7.66 ◽

2011 ◽

Vol 7 ◽

pp. 570-577 ◽

Cited By ~ 30

Author(s):

Sami F Tlais ◽

Gregory B Dudley

Keyword(s):

Transition Metal ◽

Lewis Acids ◽

Gold Catalysis ◽

Late Transition Metal ◽

Efficient Synthesis ◽

Highly Efficient ◽

Late Transition

A highly efficient synthesis of oxygenated 5,5-spiroketals was performed towards the synthesis of the cephalosporolides. Gold(I) chloride in methanol induced the cycloisomerization of a protected alkyne triol with concomitant deprotection to give a strategically hydroxylated 5,5-spiroketal, despite the potential for regiochemical complications and elimination to furan. Other late transition metal Lewis acids were less effective. The use of methanol as solvent helped suppress the formation of the undesired furan by-product. This study provides yet another example of the advantages of gold catalysis in the activation of alkyne π-systems.

An efficient synthesis of enantiomerically pure trans-2-phenylcyclohexanol

Tetrahedron Letters ◽

10.1016/s0040-4039(00)77259-5 ◽

1994 ◽

Vol 35 (31) ◽

pp. 5611-5612 ◽

Cited By ~ 33

Author(s):

S.Bruce King ◽

K.Barry Sharpless

Keyword(s):

Efficient Synthesis ◽

Enantiomerically Pure

Efficient Synthesis of Enantiomerically Pure α-Alkyl Cyclopropanecarbonitrile Derivatives from Pyrazolines†

Organic Letters ◽

10.1021/ol047937f ◽

2004 ◽

Vol 6 (26) ◽

pp. 4945-4948 ◽

Cited By ~ 32

Author(s):

José L. García Ruano ◽

Sergio A. Alonso de Diego ◽

M. Rosario Martín ◽

Esther Torrente ◽

Ana M. Martín Castro

Keyword(s):

Efficient Synthesis ◽

Enantiomerically Pure

A Simple Stereoselective Synthesis of the Cholesterol Absorption Inhibitor (-)-SCH 48461

Synthesis ◽

10.1055/s-1996-4302 ◽

1996 ◽

Vol 1996 (07) ◽

pp. 819-820 ◽

Cited By ~ 9

Author(s):

Manfred Braun ◽

Dietmar Galle

Keyword(s):

Stereoselective Synthesis ◽

Cholesterol Absorption ◽

Cholesterol Absorption Inhibitor

Simple and efficient synthesis of allo- and threo-3,3′-dimethylcystine derivatives in enantiomerically pure form

Tetrahedron Asymmetry ◽

10.1016/j.tetasy.2008.06.001 ◽

2008 ◽

Vol 19 (12) ◽

pp. 1425-1429 ◽

Cited By ~ 9

Author(s):

R.B. Nasir Baig ◽

V. Sai Sudhir ◽

Srinivasan Chandrasekaran

Keyword(s):

Pure Form ◽

Efficient Synthesis ◽

Enantiomerically Pure

ChemInform Abstract: A Novel Synthesis of the 2-Amino-1H-imidazol-4-carbaldehyde Derivatives and Its Application to the Efficient Synthesis of 2-Aminoimidazole Alkaloids, Oroidin (XIVa), Hymenidin (XIVb), Dispacamide (XVIIa), Monobromodispacamide (XVIIb),

ChemInform ◽

10.1002/chin.201101188 ◽

2010 ◽

Vol 42 (1) ◽

pp. no-no

Author(s):

Naoki Ando ◽

Shiro Terashima

Keyword(s):

Efficient Synthesis ◽

Novel Synthesis

An efficient synthesis of enantiomerically pure aromatic-fused N-containing heterocycles from common chiral aziridines

Tetrahedron ◽

10.1016/j.tet.2010.07.027 ◽

2010 ◽

Vol 66 (40) ◽

pp. 8108-8114 ◽

Cited By ~ 12

Author(s):

Jong Chan Kim ◽

Hwan Geun Choi ◽

Min Suk Kim ◽

Hyun-Joon Ha ◽

Won Koo Lee

Keyword(s):

Efficient Synthesis ◽

Enantiomerically Pure

Novel Synthesis of benzyl-Methoxyl Protected Aspalathin Analog via C-Glucosylation of Pentamethoxy Dihydropropane

Letters in Applied NanoBioScience ◽

10.33263/lianbs103.23822388 ◽

2021 ◽

Vol 10 (3) ◽

pp. 2382-2388

Keyword(s):

13C Nmr ◽

Efficient Synthesis ◽

First Report ◽

Novel Synthesis

The first report on a novel and efficient synthesis of benzyl-methoxy protected aspalathin derivative has been described via C-glucosylation of pentamethoxy dihydropropane. The synthesized compound was characterized by 1H, 13C NMR, COSY, and HSQC techniques.