A chiral pool based synthetic strategy that leads from the readily available and inexpensive C(2)-symmetric tartaric acids to the chiral O-isopropylidenebenzooxazole--a convenient precursor to the aminocyclitol core of hygromycin A as well as the chiral γ-disilyloxybutyrolactone--a pivotal intermediate to approach to the furanoside of hygromycin A.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/ol3028237 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
A Stereocontrolled Synthesis of (+)-Febrifugine via Azide and Azide-Free Pathways.
Chem Asian J
January 2025
Kasetsart University - Bangkhen Campus: Kasetsart University, Chemistry, 50, Department of Chemistry, Faculty of Science, Kasetsart UNiversity, Ladyao, Chatu, 10900, Bangkok, THAILAND.
(+)-Febrifugine, a natural antimalarial compound with a promising therapeutic profile, has become a hot target for synthetic chemists seeking to optimize its biological activity and expand its therapeutic applications. In this research, we present a stereocontrolled synthesis of (+)-febrifugine using both azide and azide-free approaches. Starting from the commercially available chiral pool precursor, d-glucose, the synthesis was completed in 20 steps for both approaches.
View Article and Find Full Text PDFSelection of a Fluorinated Aptamer Targeting the Viral RNA Frameshift Element with Different Chiralities.
Biochemistry
January 2025
Department of Biochemistry and Molecular Biology, Melvin and Bren Simon Cancer Center, Indiana University School of Medicine, Indianapolis, Indiana 46202, United States.
The development of RNA aptamers with high specificity and affinity for target molecules is a critical advancement in the field of therapeutic and diagnostic applications. This study presents the selection of a 2'-fluoro-modified mirror-image RNA aptamer through the in vitro SELEX process. Using a random RNA library, we performed iterative rounds of selection and amplification to enrich aptamers that bind specifically to the viral attenuator hairpin RNA containing the opposite chirality, which is an important part of the frameshift element.
View Article and Find Full Text PDFRecent advances in the development of enantiopure BODIPYs and some related enantiomeric compounds.
Chem Commun (Camb)
January 2025
Department of Chemistry, Khalifa University, SAN Campus, Abu Dhabi, United Arab Emirates.
Article Synopsis
- Small chiral organic dyes, especially chiral variants of boron dipyrromethene (BODIPY), are important for developing advanced smart chiroptical luminophores due to their outstanding photophysical properties.
- Recent research has focused on inducing chirality in achiral BODIPY by creating chiral centers at various positions, enhancing synthetic accessibility.
- The developments in chiral BODIPY have potential applications in fields such as photodynamic therapy, bio-imaging, optoelectronics, and more.
Studies on the Stereoselective Synthesis of Sacubitril via a Chiral Amine Transfer Approach.
Chem Asian J
December 2024
Organic Chemistry Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune, 411008, India.
We present a comprehensive account of our efforts directed towards the synthesis of sacubitril, a neprilysin inhibitor used in combination with valsartan and marketed as Entresto™. Our initial approach to the formal synthesis of sacubitril employed a chiral pool strategy, utilizing (S)-pyroglutamic acid as a key building block and Cu(I)-mediated Csp-Csp cross-coupling as a key transformation. Further investigations led to the development of chiral amine transfer (CAT) reagents-based stereoselective synthesis.
View Article and Find Full Text PDFMicrobe Engineering to Provide Drimane-Type Building Blocks for Chiral Pool Synthesis of Meroterpenoids.
Angew Chem Int Ed Engl
December 2024
State Key Laboratory of Natural Medicines, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing, 211198, China.
Drimane-type merosesquiterpenoids (DMT) are a class of natural products with diverse structures and broad biological activity. Classical DMT synthesis relies on atom-inefficient plant-derived chiral pool building blocks, while alternative drimane-type building blocks such as drimenol and albicanol offer more direct routes but face production challenges. In this study, we engineered a microbial platform for efficient production of these building blocks.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!