Total Synthesis of (−)-FR182877 through Tandem IMDA-IMHDA Reactions and Stereoselective Transition-Metal-Mediated Transformations

2009 ◽  
Vol 48 (14) ◽  
pp. 2580-2583 ◽  
Author(s):  
Natsumi Tanaka ◽  
Takahiro Suzuki ◽  
Takehiko Matsumura ◽  
Yosuke Hosoya ◽  
Masahisa Nakada
Keyword(s):  
Transition Metal ◽  
Total Synthesis

Toward the total synthesis of lophotoxin — New methodologies and synthetic strategies

2006 ◽  
Vol 84 (10) ◽  
pp. 1226-1241 ◽  
Author(s):  
Peter Wipf ◽  
Michel Grenon
Keyword(s):  
Transition Metal ◽  
Total Synthesis ◽  
Recent Progress ◽  
Furan Ring ◽  
Addition Reaction ◽  
Thermal Conditions ◽  
Preliminary Results ◽  
Keto Esters ◽  
New Methodologies ◽  
Metal Catalyzed

Our recent progress toward the synthesis of the furanocembranolide lophotoxin (1) is disclosed. Strategies for the stereoselective incorporation of the C13 stereocenter by a catalytic desymmetrization of a cyclic meso-anhydride, as well as a novel 1,6-addition reaction of organocuprates to unsaturated [1,3]dioxin-4-ones are discussed. Preliminary results on the development of a rhodium-catalyzed asymmetric 1,6-addition reaction are also mentioned. Finally, modifications of a previously reported transition-metal-catalyzed cyclization reaction involving α-propargyl β-keto esters allow furan ring formation either under thermal conditions or by microwave irradiation.Key words: 1,6-addition, organocuprates, catalytic desymmetrization, furan cyclization, microwave.

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.

Transition-Metal-Catalyzed Reactions Involving Arynes

Synthesis ◽  
2017 ◽  
Vol 50 (01) ◽  
pp. 1-16 ◽  
Author(s):  
Santosh Mhaske ◽  
Ranjeet Dhokale
Keyword(s):  
Natural Products ◽  
Transition Metal ◽  
Total Synthesis ◽  
Scientific Community ◽  
Multicomponent Reactions ◽  
Polycyclic Aromatic Compounds ◽  
Polycyclic Aromatic ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

The plethora of transformations attainable by the transition-metal-catalyzed reactions of arynes has found immense contemporary interest in the scientific community. This review highlights the scope and importance of transition-metal-catalyzed aryne reactions in the field of synthetic organic chemistry reported to date. It covers transformations achieved by the combination of arynes and various transition metals, which provide a facile access to a biaryl motif, fused polycyclic aromatic compounds, different novel carbocycles, various heterocycles, and complex natural products.1 Introduction2 Insertion of Arynes3 Annulation of Arynes4 Cycloaddition of Arynes5 Multicomponent Reactions of Arynes6 Miscellaneous Reactions of Arynes7 Total Synthesis of Natural Products Using Arynes8 Conclusion

scholarly journals Transition metal catalyzed stereodivergent synthesis of syn- and anti-δ-vinyl-lactams: formal total synthesis of (−)-cermizine C and (−)-senepodine G

2019 ◽  
Vol 10 (10) ◽  
pp. 3074-3079 ◽  
Author(s):  
Johannes Philipp Schmidt ◽  
Bernhard Breit
Keyword(s):  
Transition Metal ◽  
Total Synthesis ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

A stereodivergent and diastereoselective transition-metal-catalyzed intramolecular hydroamidation of allenes and alkynes furnishing δ-vinyl-lactams is reported.

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