scholarly journals Efficient Construction of the Hexacyclic Ring Core of Palau’amine: The pKa Concept for Proceeding with Unfavorable Equilibrium Reactions

2021 ◽  
Author(s):  
Eisaku Ohashi ◽  
Sangita Karanjit ◽  
Atsushi Nakayama ◽  
Kohei Takeuchi ◽  
Sherif Emam ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Molecular Architecture ◽  
Immunosuppressive Activity ◽  
Equilibrium Reactions ◽  
Efficient Construction ◽  
Ring Core ◽  
Synthetic Target

Palau’amine has received a great deal of attention as an attractive synthetic target due to its intriguing molecular architecture and significant immunosuppressive activity, and we achieved its total synthesis in...

scholarly journals New cyclization reactions in organic syntheses

2002 ◽  
Vol 74 (1) ◽  
pp. 159-166 ◽  
Author(s):  
Iwao Ojima
Keyword(s):  
Amino Acids ◽  
Transition Metal ◽  
Total Synthesis ◽  
Cyclization Reactions ◽  
Organic Syntheses ◽  
Carbocyclic Compounds ◽  
Efficient Construction ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Recent development in the transition metal-catalyzed cyclization reactions for organic syntheses in the author's laboratories is summarized, which includes (i) novel silylcarbocyclizations (SiCaCs) and carbonylative carbotricyclizations, (ii) intramolecular silylformylations and desymmerization of siloxydiynes by sequential double silylformylation, (iii) efficient total synthesis of (+)-prosopinine, (iv) enantioselective desymmetrization of aminodienes, and (iv) new and efficient routes to 1-azabicyclo[x.y.0]alkane amino acids. All these processes are catalyzed by Rh or Rh­Co complexes, and useful for rapid and efficient construction of a variety of heterocyclic and carbocyclic compounds. Mechanisms of these new carbocyclization and cyclohydrocarbonylation reactions are also discussed.

scholarly journals Total Synthesis of the Reported Structure of Cahuitamycin A

2020 ◽  
Author(s):  
Justin Shapiro ◽  
Savannah Post ◽  
William Wuest
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Twelve Step ◽  
Target Compound ◽  
New Family ◽  
Iron Trafficking ◽  
Linear Sequence ◽  
Alternative Structure ◽  
Synthetic Target

In a 2016 screen of natural product extracts a new family of natural products, the cahuitamycins, was discovered and found to inhibit the formation of biofilms in the human pathogen <i>Acinetobacter baumannii</i>. The molecules contain an unusual piperazate residue that raises structure/function and biosynthesis questions and resemble iron-trafficking virulence factors from <i>A. baumannii</i>, suggesting a connection between metal homeostasis and biofilm-mediated pathogenicity. Here we disclose the first total synthesis of the reported structure of cahuitamycin A in a twelve-step longest linear sequence and 18% overall yield. Comparison of spectral data of the authentic natural product and synthetic target compound demonstrate that the reported structure is distinct from the isolated metabolite. Herein, we propose an alternative structure to reconcile our findings with the isolation report, setting the stage for future synthetic and biochemical investigations of an important class of natural products.

Studies Toward the Total Synthesis of (-)-Kampanol A (II): An Efficient Construction of the ABCD Ring System (I).

ChemInform ◽  
2003 ◽  
Vol 34 (4) ◽  
Author(s):  
Katsuhiko Iwasaki ◽  
Mari Nakatani ◽  
Munenori Inoue ◽  
Tadashi Katoh
Keyword(s):  
Total Synthesis ◽  
Ring System ◽  
Efficient Construction

Total synthesis of (−)-ephedradine A: an efficient construction of optically active dihydrobenzofuran-ring via C–H insertion reaction

Tetrahedron ◽  
2004 ◽  
Vol 60 (43) ◽  
pp. 9615-9628 ◽  
Author(s):  
Wataru Kurosawa ◽  
Hideki Kobayashi ◽  
Toshiyuki Kan ◽  
Tohru Fukuyama
Keyword(s):  
Total Synthesis ◽  
Optically Active ◽  
Insertion Reaction ◽  
Efficient Construction

scholarly journals Concise Total Synthesis of Trichodermamides A, B, and C Enabled by an Efficient Construction of the 1,2-Oxazadecaline Core

2015 ◽  
Vol 137 (25) ◽  
pp. 8050-8053 ◽  
Author(s):  
Adelphe M. Mfuh ◽  
Yu Zhang ◽  
David E. Stephens ◽  
Anh X. T. Vo ◽  
Hadi D. Arman ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Efficient Construction
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