+ Resolve Article
+ Follow Us
Follow on FacebookFollow on Facebook
Follow on TwitterFollow on Twitter

+ Translate
+ Subscribe to Site Feed
GeoScience Most Shared ContentMost Shared Content

Building constrained peptidomimetics: A convenient approach to 3-phenyl-5-vinyl substituted proline derivatives

, : Building constrained peptidomimetics: A convenient approach to 3-phenyl-5-vinyl substituted proline derivatives. Tetrahedron 57(30): 6407-6415, 23 July

An approach to the synthesis of 3-phenyl-5-vinyl substituted prolines starting from readily available 2,3-disubstituted pentenoic acid derivatives is reported. The route converts the pentenoic acid derived starting materials into cyclic N-acyliminium ion precursors with the use of a hydroboration-Swern oxidation sequence. This overall transformation worked best when the initial alkylborane product was treated sequentially with excess MCPBA and then acetone prior to the Swern oxidation. In this way, a 70% yield of the desired N-acyliminium ion precursor could be obtained. Once in hand, the cyclic N-acyliminium ion precursor was used to make the desired 3-phenyl-5-vinyl substituted prolines.


DOI: 10.1016/s0040-4020(01)00532-4

Other references

Kwak, D.; Wu, Y.; Horbett, T.A., 2005: Fibrinogen and von Willebrand's factor adsorption are both required for platelet adhesion from sheared suspensions to polyethylene preadsorbed with blood plasma. Previous studies showed that platelet adhesion to biomaterials from static suspensions was greatly increased by the adsorption of even very small amounts (< 5 ng/cm(2)) of fibrinogen (Fg). In this study, the sensitivity of platelet adhesion to...

López, Mía.; Dosal, A.; Villoria, A.; Moreno, L.; Calvet, X., 2015: A nurse-driven outpatient clinic for thiopurine-treated inflammatory bowel disease patients reduces physician visits and increases follow-up efficiency. Patients on thiopurine therapy need frequent monitoring to prevent drug adverse events. To describe the structure and main results of a nurse-driven outpatient clinic (NDOC) program for the follow-up of patients receiving treatment with thiopurine...

Goponenko, A.V.; Dzenis, Y.A., 2017: Role of Mechanical Factors in Applications of Stimuli-Responsive Polymer Gels - Status and Prospects. Due to their unique characteristics such as multifold change of volume in response to minute change in the environment, resemblance of soft biological tissues, ability to operate in wet environments, and chemical tailorability, stimuli responsive...

E.S.avridou; K.T.orup-Kristensen; S.D.Y.ung, 2011: Assessment of selenium mineralization and availability from catch crops. Selenium (Se) release from four plant species (Indian mustard, fodder radish, Italian ryegrass and hairy vetch) was measured under controlled leaching conditions and in a pot incubation experiment as part of a study of the potential for using thes...

Ackroyd-Stolarz, S.; MacKinnon, N.J.; Zed, P.J.; Murphy, N., 2011: Use of an electronic information system to identify adverse events resulting in an emergency department visit. There is limited information about the nature of adverse events (AEs) that necessitate an emergency department (ED) visit. The objective of the current study was to demonstrate the feasibility of using routinely collected electronic data to identi...

Ludi, W., 1958: Report of the 11th course in alpine botany. Account of a week's excursion in the eastern Alps with appended phytosociological analyses of some communities.

Keller A.; Iriki A.; Asanuma H., 1989: Induction of ltp by activation of corticocortical inputs to the motor cortex intracellular recordings and labeling. Society for Neuroscience Abstracts 15(1): 280

Ondrisik, P.; Noskovic, J.; Rakovska, A., 2001: The influence of magnesite emissions on changes in pH. The influence of captured magnesite emissions on changes in soil reaction of very acid soil was tested in laboratory conditions. Dried up, homogenized soil of Dystric Cambisol humus horizon (8kg), passed through a 5.00 mm sieve, was placed into ex...

Spitzer, R.L., 1999: Harmful dysfunction and the DSM definition of mental disorder. Physicians, including psychiatrists, give a lot of thought in their everyday work to answer the question of whether or not a particular patient has a disorder; they rarely give much thought to the broader issue of what constitutes a disorder. Rema...

Coudert J.M.; Lejeune J.M.; Rojas J.; Varet J., 1985: Normal-gradient geothermal energy; technical and economic characteristics. Pages 77-84: