105262-86-0Relevant academic research and scientific papers
Synthesis of New Benzocyclotrimer Analogues: New Receptors for Tetramethylammonium Ion Recognition
Carrillo, Romen,Hynes, Michael J.,Martín, Víctor S.,Martín, Tomás,Crisóstomo, Fernando Pinacho
, p. 2912 - 2915 (2015)
Using a [2 + 2 + 2] cycloaddition/Mitsunobu reaction sequence, a convenient synthesis to access new benzocyclotrimer analogues has been developed. The new receptors have the geometry and functionality capable of recognizing the tetramethylammonium ion in
Multidentate triphenolsilane-based alkyne metathesis catalysts
Yang, Haishen,Liu, Zhenning,Zhang, Wei
, p. 885 - 890 (2013)
A series of triphenolsilane-coordinated molybdenum(VI) propylidyne catalysts has been developed, which are resistant to small alkyne polymerization and compatible with various functional groups (including phenol substrates). The catalysts remain active in
Synthetic Studies of the Rubellin Natural Products: Development of a Stereoselective Strategy and Total Synthesis of (+)-Rubellin C
Gartman, Jackson A.,Tambar, Uttam K.
, p. 11237 - 11262 (2021/08/16)
This manuscript describes our studies of the class of natural products known as the rubellins, culminating in the total synthesis of (+)-rubellin C. These anthraquinone-based natural products contain a variety of stereochemical and architectural motifs, including a 6-5-6-fused ring system, 5 stereogenic centers, and a central quaternary center. Herein, we report our development of a strategy to target the stereochemically dense core and anthraquinone nucleus, including approaches such as a bifunctional allylboron and vinyl triflate reagent, an anthraquinone benzylic metalation strategy, and a late-stage anthraquinone introduction strategy. Our studies culminate in a successful route to highly functionalized anthraquinone-based natural product scaffolds and a stereoselective total synthesis of (+)-rubellin C. These strategies and outcomes will aid in synthetic planning toward anthraquinone-based natural products of high interest.
Total Synthesis of (+)-Rubellin C
Gartman, Jackson A.,Tambar, Uttam K.
, p. 9145 - 9150 (2020/08/24)
The rubellins are a family of stereochemically complex anthraquinoid heterodimers containing an unprecedented chemical scaffold. Although the rubellins have been known for over three decades, no total synthesis has been achieved since their discovery. The
Asymmetric synthesis of novel spirocycles via a chiral phosphoric acid catalyzed desymmetrization
Kelley, Amber M.,Minerali, Eni,Wilent, Jennifer E.,Chambers, Nicholas J.,Stingley, Kyla J.,Wilson, G. Tyler,Petersen, Kimberly S.
, p. 1262 - 1264 (2019/04/10)
A straightforward method for the asymmetric preparation of novel lactone and lactam spirocycles is described. An initial desymmetrization via a chiral Br?nsted acid yields enantioenriched lactones which readily undergo a second cyclization to give the des
Diverse ring opening of thietanes and other cyclic sulfides: An electrophilic aryne activation approach
Zheng, Tianyu,Tan, Jiajing,Fan, Rong,Su, Shuaisong,Liu, Binbin,Tan, Chen,Xu, Kun
, p. 1303 - 1306 (2018/02/14)
Organosulfides are a common class of structure units in bioactive molecules and functional materials motivating continuous developments of efficient synthetic methods. Herein, we report an electrophilic aryne-activated ring opening protocol of one or two
Gold-Catalyzed Oxidative Coupling of Alkynes toward the Synthesis of Cyclic Conjugated Diynes
Ye, Xiaohan,Peng, Haihui,Wei, Chiyu,Yuan, Teng,Wojtas, Lukasz,Shi, Xiaodong
, p. 1983 - 1993 (2018/10/02)
Gold-catalyzed oxidative coupling of alkynes was developed as an efficient approach for the synthesis of challenging cyclic conjugated diynes (CCD). Compared with the classic copper-promoted oxidative coupling reaction of alkynes, this gold-catalyzed process exhibited a faster reaction rate due to rapid reductive elimination from the Au(III) intermediate. This unique reactivity thus allowed a challenging diyne macrocyclization to take place with high efficiency. Condition screening revealed an [(n-Bu)4N]+[Cl-Au-Cl]? salt as the optimal pre-catalyst. Macrocycles with ring size between 13 and 28 atoms were prepared in moderate to good yields, which highlighted the broad substrate scope of this new strategy. Furthermore, the synthetic utilities of the CCDs for copper-free click chemistry have been demonstrated, showcasing the potential application of this strategy in biological systems. Macrocycles are important structural moieties in medicinal and biological research, and efficient methods for macrocyclization are always in high demand. With the unique conformation having six carbon atoms in a linear geometry, the cyclic conjugated diynes (CCD) present greater synthetic challenges and have been much less explored. Therefore, application of these unique macrocycles in biological studies is largely unexplored. Here, we describe the discovery of gold-catalyzed Glaser-Hay type oxidative coupling of terminal alkynes to achieve CCD under diluted conditions with broad substrate scope and great functional group compatibility. Taking advantage of the 14-member cyclic diyne, a copper-free click chemistry was achieved, which provided an effective alternative strategy for the traditional cyclooctyne-based azide-alkyne cycloaddition, suggesting a promising future for this method in tackling challenging problems in related biological and medicinal research. Gold-catalyzed oxidative coupling of alkynes was developed as an efficient approach for the synthesis of challenging cyclic conjugated diyne. Compared with copper-promoted oxidative coupling, this protocol allowed macrocyclization under dilute conditions with good overall reactivity and high functional group tolerance. The success in achieving copper-free click chemistry on cyclic conjugated diyne highlights its potential application in biological and medicinal research.
7-MEMBERED FUSED HETEROCYCLES AND METHODS OF THEIR SYNTHESIS
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, (2015/03/16)
Disclosed are a new method for synthesizing 7-membered fused heterocycles and compounds synthesized by the new method. The method involves a dual activation strategy using an N-heterocyclic carbene catalyst as a first Lewis base and another second Lewis b
Highly Active Multidentate Catalysts for Efficient Alkyne Metathesis
-
, (2013/10/08)
The invention relates to highly active and selective catalysts for alkyne metathesis. In one aspect, the invention includes a multidentate organic ligand wherein one substrate-binding site of the metal center is blocked. In another aspect, the invention includes N-quaternized or silane-based multidentate organic ligands, capable of binding to metals. In yet another aspect, the invention includes N-quaternized or silane-based multidentate catalysts. The catalysts of the invention show high robustness, strong resistance to small alkyne polymerization and significantly enhanced catalytic activity compared to their corresponding non-quaternized or non-silane-based multidentate catalyst analogues.
A dual Lewis base activation strategy for enantioselective carbene-catalyzed annulations
Izquierdo, Javier,Orue, Ane,Scheidt, Karl A.
supporting information, p. 10634 - 10637 (2013/08/23)
A dual activation strategy integrating N-heterocyclic carbene (NHC) catalysis and a second Lewis base has been developed. NHC-bound homoenolate equivalents derived from α,β-unsaturated aldehydes combine with transient reactive o-quinone methides in an ena
