141567-53-5Relevant articles and documents
Total synthesis of the virginiamycin antibiotic 14,15-anhydropristinamycin IIB
Entwistle, David A.,Jordan, Stuart I.,Montgomery, John,Pattenden, Gerald
, p. 1315 - 1317 (1996)
A total synthesis of the virginiamycin 14,15-anhydropristinamycin IIB 16 has been achieved from chiral, non-racemic starting materials, and using a route which features an intramolecular Stille coupling reaction, viz. 14→15, as the key stratagem. The virginiamycin 16 was identical with an authentic sample produced from a Streptomyces fermentation process.
Total synthesis of oxazole-based virginiamycin antibiotics: 14,15- Anhydropristinamycin II(B)
Entwistle, David A.,Jordan, Stuart I.,Montgomery, John,Pattenden, Gerald
, p. 603 - 612 (1998)
A total synthesis of 14,15-anhydropristinamycin II(B) (3), a member of the virginiamycin family of antibiotics (also known as streptogramins, pristinamycins or synergimycins) produced by STreptomyces is described. The synthesis is achieved from chiral, non-racemic starting materials and uses a convergent route involving synthesis of the substituted proline 7 and the 4- oxazole carboxylic acid 8, their coupling to the vinylstannane substituted vinyl bromide 6, and finally an intramolecular sp2-sp2 Stille coupling reaction, i.e. 6 → 22, to elaborate the macrocyclic core of the natural product.
AZIRIDINE CONTAINING EPOTHILONE ANALOGS, METHODS OF SYNTHESIS, METHODS OF TREATMENT, AND DRUG CONJUGATES
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Page/Page column 107, (2018/11/10)
In one aspect, the present disclosure provides epothilone analogs of the formula: (I) wherein the variables are as defined herein. In another aspect, the present disclosure also provides methods of preparing the compounds disclosed herein. In another aspect, the present disclosure also provides pharmaceutical compositions and methods of use of the compounds disclosed herein. Additionally, drug conjugates with cell targeting moieties of the compounds are also provided.
12,13-Aziridinyl Epothilones. Stereoselective Synthesis of Trisubstituted Olefinic Bonds from Methyl Ketones and Heteroaromatic Phosphonates and Design, Synthesis, and Biological Evaluation of Potent Antitumor Agents
Nicolaou,Rhoades, Derek,Wang, Yanping,Bai, Ruoli,Hamel, Ernest,Aujay, Monette,Sandoval, Joseph,Gavrilyuk, Julia
supporting information, p. 7318 - 7334 (2017/06/06)
The synthesis and biological evaluation of a series of 12,13-aziridinyl epothilone B analogues is described. These compounds were accessed by a practical, general process that involved a 12,13-olefinic methyl ketone as a starting material obtained by ozonolytic cleavage of epothilone B followed by tungsten-induced deoxygenation of the epoxide moiety. The attachment of the aziridine structural motif was achieved by application of the Ess-Kürti-Falck aziridination, while the heterocyclic side chains were introduced via stereoselective phosphonate-based olefinations. In order to ensure high (E) selectivities for the latter reaction for electron-rich heterocycles, it became necessary to develop and apply an unprecedented modification of the venerable Horner-Wadsworth-Emmons reaction, employing 2-fluoroethoxyphosphonates that may prove to be of general value in organic synthesis. These studies resulted in the discovery of some of the most potent epothilones reported to date. Equipped with functional groups to accommodate modern drug delivery technologies, some of these compounds exhibited picomolar potencies that qualify them as payloads for antibody drug conjugates (ADCs), while a number of them revealed impressive activities against drug resistant human cancer cells, making them desirable for potential medical applications.
PYRROLE ANTIFUNGAL AGENTS
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, (2009/12/05)
The invention provides compounds of formula (I), and pharmaceutically and agriculturally acceptable salts thereof; wherein: R1, R2, R3, R4, R5, R6, A1, L1 and n are as defined herein. These compounds and their pharmaceutically acceptable salts are useful in prevention or treatment of a fungal disease. Compounds of formula (I), and agriculturally acceptable salts thereof, may also be used as agricultural fungicides.
Large-scale preparation of 2-methyloxazole-4-carboxaldehyde
Benoit, Georges-Emmanuel,Carey, John S.,Chapman, Alan M.,Chima, Ranjit,Hussain, Nigel,Popkin, Matthew E.,Roux, Guillaume,Tavassoli, Bahareh,Vaxelaire, Carine,Webb, Michael R.,Whatrup, David
, p. 88 - 95 (2012/12/31)
The large-scale preparation of 2-methyloxazole-4-carboxaldehyde presents a significant challenge due to the physical characteristics of the molecule. A method for the preparation of 10-kg batches of 2-methyloxazole-4-carboxaldehyde is described. The key reaction is the reduction of the corresponding N-methoxy-N-methyl amide using lithium aluminium hydride, followed by workup and isolation by crystallization.
Amino-Containing Compounds Which Inhibit Memapsin 2 Beta-Secretase Activity and Methods of Use Thereof
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Page/Page column 20, (2008/12/05)
The present invention provides novel beta-secretase inhibitors and methods for their use, including methods of treating of Alzheimer's disease.
Oxidative rearrangements of isobenzofurans: Studies toward the synthesis of the ajudazols
Hobson, Stephen J.,Parkin, Andrew,Marquez, Rodolfo
supporting information; experimental part, p. 2813 - 2816 (2009/05/27)
(Chemical Equation Presented) We present a new facet of isobenzofuran chemistry which allows for its efficient manipulation to generate biologically relevant entities. This methodology has been successfully applied toward the synthesis of ajudazol A.
CASPASE INHIBITORS BASED ON PYRIDAZINONE SCAFFOLD
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Page/Page column 51, (2008/06/13)
The present invention relates to a pyridazinone derivative which can be used as a caspase inhibitor, process for the preparation thereof, and pharmaceutical composition for inhibiting caspase comprising the same.
A stereoselective synthesis of the C20-C32 fragment of the phorboxazoles
Yadav,Satyanarayana,Srinivasulu,Kunwar
, p. 1577 - 1580 (2008/02/04)
The C20-C32 fragment of the phorboxazoles was realized in a stereoconvergent manner utilizing a desymmetrization approach. This successful strategy involves epimerization and modified Julia olefination as key steps. Georg Thieme Verlag Stuttgart.