1193-47-1Relevant articles and documents
First total synthesis and assignment of the stereochemistry of crispatenine
Bourdron, Julien,Commeiras, Laurent,Audran, Gerard,Vanthuyne, Nicolas,Hubaud,Parrain, Jean-Luc
, p. 3770 - 3775 (2007)
(Figure Presented) The first racemic and enantioselective synthesis of crispatenine 1 has been achieved, which involved a few steps, enabling the assignment of the absolute and relative configurations.
Baldwin,J.E.,Kruse,L.I.
, p. 233 - 235 (1977)
Sequential hydroformylation/aldol addition reactions of β,γ- unsaturated ketones and their derivatives
Hollmann, Christoph,Eilbracht, Peter
, p. 4313 - 4316 (1999)
Novel rhodium(I) complex catalysed tandem hydroformylation/aldol reactions of a β,γ-unsaturated ketone 1 or its silyl enol ethers 4 in a one-pot procedure are presented to give varying cyclisation products depending on the reaction conditions.
Sisti
, p. 3305 (1970)
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Sisti,A.J.,Vitale,A.C.
, p. 4090 - 4094 (1972)
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Bailey,Madoff
, p. 2707 (1954)
Stereoselective Synthesis of 1-Tuberculosinyl Adenosine; A Virulence Factor of Mycobacterium tuberculosis
Buter, Jeffrey,Heijnen, Dorus,Wan, Ieng Chim,Bickelhaupt, F. Matthias,Young, David C.,Otten, Edwin,Moody, D. Branch,Minnaard, Adriaan J.
, p. 6686 - 6696 (2016)
Despite its status as one of the world's most prevalent and deadly bacterial pathogens, Mycobacterium tuberculosis (Mtb) infection is not routinely diagnosed by rapid and highly reliable tests. A program to discover Mtb-specific biomarkers recently identified two natural compounds, 1-tuberculosinyl adenosine (1-TbAd) and N6-tuberculosinyl adenosine (N6-TbAd). Based on their association with virulence, the lack of similar compounds in nature, the presence of multiple stereocenters, and the need for abundant products to develop diagnostic tests, synthesis of these compounds was considered to be of high value but challenging. Here, a multigram-scale stereoselective synthesis of 1-TbAd and N6-TbAd is described. As a key-step, a chiral auxiliary-mediated Diels-Alder cycloaddition was developed, introducing the three stereocenters with a high exo endo ratio (10:1) and excellent enantioselectivity (>98% ee). This constitutes the first entry into the stereoselective synthesis of diterpenes with the halimane skeleton. Computational studies explain the observed stereochemical outcome.
5-MEMBERED HETEROARYLAMINOSULFONAMIDES FOR TREATING CONDITIONS MEDIATED BY DEFICIENT CFTR ACTIVITY
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Page/Page column 366, (2021/05/21)
The invention relates to heteroaryl compounds, pharmaceutically acceptable salts thereof, and pharmaceutical preparations thereof. Also described herein are compositions and the use of such compounds in methods of treating diseases and conditions mediated by deficient CFTR activity, in particular cystic fibrosis.
(Poly)cationic λ3-Iodane-Mediated Oxidative Ring Expansion of Secondary Alcohols
Walters, Jennifer C.,Tierno, Anthony F.,Dubin, Aimee H.,Wengryniuk, Sarah E.
supporting information, p. 1460 - 1464 (2018/04/06)
Herein, a simplified approach to the synthesis of medium-ring ethers through the electrophilic activation of secondary alcohols with (poly)cationic λ3-iodanes (N-HVIs) is reported. Excellent levels of selectivity are achieved for C–O bond migration over established α-elimination pathways, enabled by the unique reactivity of a novel 2-OMe-pyridine-ligated N-HVI. The resulting hexafluoroisopropanol (HFIP) acetals are readily derivatized with a range of nucleophiles, providing a versatile functional handle for subsequent manipulations. The utility of this methodology for late-stage natural product derivatization was also demonstrated, providing a new tool for diversity-oriented synthesis and complexity-to-diversity (CTD) efforts. Preliminary mechanistic investigations reveal a strong effect of alcohol conformation on the reactive pathway, thus providing a predictive power in the application of this approach to complex molecule synthesis.