Journal ArticleDOI
A new general method for preparation of N-methoxy-N-methylamides. Application in direct conversion of an ester to a ketone
J. Michael Williams,Ronald B. Jobson,Nobuyoshi Yasuda,G. Marchesini,Ulf-H. Dolling,Edward J. J. Grabowski +5 more
Reads0
Chats0
TLDR
In this article, the azasteroid 5α-reductase inhibitor MK-0434 is described for the direct conversion of a highly hindered ester to a ketone, and the reaction of an ester with N, O -dimethylhydroxylamine and a suitable organomagnesium reagent or lithium amide base is described.About:
This article is published in Tetrahedron Letters.The article was published on 1995-07-31. It has received 198 citations till now. The article focuses on the topics: Lithium amide & Ketone.read more
Citations
More filters
Journal ArticleDOI
Synthesis of Amides from Esters and Amines with Liberation of H2 under Neutral Conditions
TL;DR: A mechanism is proposed involving metal-ligand cooperation via aromatization-dearomatization of the pyridine moiety and hemilability of the amine arm ofThe pincer ligand, achieving efficient synthesis of amides directly from esters and amines with the liberation of molecular hydrogen.
Journal ArticleDOI
Identification of a Benzoisoxazoloazepine Inhibitor (CPI-0610) of the Bromodomain and Extra-Terminal (BET) Family as a Candidate for Human Clinical Trials.
Brian K. Albrecht,Victor S. Gehling,Michael C. Hewitt,Rishi G. Vaswani,Alexandre Côté,Yves Leblanc,Christopher G. Nasveschuk,Steve Bellon,Louise Bergeron,Robert M. Campbell,Nico Cantone,Michael R. Cooper,Richard T. Cummings,Hariharan Jayaram,Shivangi Joshi,Jennifer A. Mertz,Adrianne Neiss,Emmanuel Normant,Michael O'Meara,Eneida Pardo,Florence Poy,Peter Sandy,Jeffrey G. Supko,Robert J. Sims,Jean-Christophe Harmange,Alexander M. Taylor,James E. Audia +26 more
TL;DR: A potent and selective benzoisoxazoloazepine BET bromodomain inhibitor is described that attenuates BET-dependent gene expression in vivo, demonstrates antitumor efficacy in an MV-4-11 mouse xenograft model, and is currently undergoing human clinical trials for hematological malignancies.
Journal ArticleDOI
Design and stereoselective preparation of a new class of chiral olefin metathesis catalysts and application to enantioselective synthesis of quebrachamine: catalyst development inspired by natural product synthesis.
TL;DR: St stereogenic-at-Mo complexes bearing only monodentate ligands have been designed and provide significantly higher levels of activity than observed with the previously reported Ru- or Mo-based complexes.
Journal ArticleDOI
Enantioselective total synthesis of altohyrtin c (spongistatin 2)
David A. Evans,B. Wesley Trotter,Paul J. Coleman,Cote Bernard,Luiz C. Dias,Hemaka A. Rajapakse,Andrew N. Tyler +6 more
TL;DR: The first total synthesis of a spongipyran macrolide, altohyrtin C, was described in this paper, which relies on a regioselective macrolactonization, a stere-lective Wittig coupling of the two major synthetic fragments, a complex anti-aldol reaction to join the C1-C15 and C16-C28 spiroketal regions, and an anomeric sulfone acylation to join C29-C37 and C38-C43 pyran regions.
Journal ArticleDOI
Direct Synthesis of Amides by Dehydrogenative Coupling of Amines with either Alcohols or Esters: Manganese Pincer Complex as Catalyst
Amit Kumar,Noel Angel Espinosa-Jalapa,Gregory Leitus,Yael Diskin-Posner,Liat Avram,David Milstein +5 more
TL;DR: The first example of base-metal-catalysed synthesis of amides from the coupling of primary amines with either alcohols or esters is reported, making the overall process atom-economical and sustainable.
References
More filters
Journal ArticleDOI
N-methoxy-n-methylamides as effective acylating agents
Steven Nahm,Steven M. Weinreb +1 more
TL;DR: Readily preparable N-methoxy-N-methylamides couple in good yields with Grignard and organolithium reagents to produce ketones, and are reduced with hydrides to afford aldehydes.
Journal ArticleDOI
The effect of finasteride in men with benign prostatic hyperplasia. The Finasteride Study Group.
Glenn J. Gormley,Elizabeth Stoner,Reginald C. Bruskewitz,Julianne Imperato-McGinley,Patrick C. Walsh,John D. McConnell,Gerald L. Andriole,Jack Geller,Bruce Bracken,J S Tenover +9 more
TL;DR: The effect of finasteride (1 mg and 5 mg) on prostate hyperplasia was evaluated in 895 men with prostate cancer in a double-blind study as discussed by the authors.
Journal ArticleDOI
Contrasteric carboximide hydrolysis with lithium hydroperoxide
TL;DR: In this article, the use of lithium hydroperoxide for the highly regioselective hydrolysis of a range of carboximides is described, and several cases are provided where the reagent exhibited dramatically different than the complementary reactions with hydroxide.
Journal ArticleDOI
Azasteroids: structure-activity relationships for inhibition of 5.alpha.-reductase and of androgen receptor binding
Gary H. Rasmusson,Glenn F. Reynolds,Nathan G. Steinberg,Edward Walton,Gool F. Patel,Tehming Liang,Margaret A. Cascieri,Anne H. Cheung,J. R. Brooks,Charles Berman +9 more
TL;DR: A series of steroids were prepared and tested in vitro as inhibitors of human and rat prostatic 5 alpha-reductase and of binding of dihydrotestosterone to the rat androgen receptor and the primary structural modifications were changes of the A ring and of moieties attached at the C-17 position of the steroid nucleus.
Journal ArticleDOI
An Alternative Procedure for the Aluminum-Mediated Conversion of Esters to Amides
TL;DR: In this paper, a method was developed for directly converting esters to amides using reagents derived from the reaction of trimethylaluminum with ammonium chloride, methylamine hydrochloride or dimethylamine hydchloride.