A transition metal-catalyzed enyne metathesis for the preparation of pyrrolizidine alkaloid core: Application towards the total synthesis of stemaphylline

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.

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Transition-Metal-Catalyzed Reactions Involving Arynes

Synthesis ◽

10.1055/s-0036-1589517 ◽

2017 ◽

Vol 50 (01) ◽

pp. 1-16 ◽

Cited By ~ 25

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

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Combined Directed Remote Metalation−Transition Metal Catalyzed Cross Coupling Strategies: The Total Synthesis of the Aglycones of the Gilvocarcins V, M, and E and Arnottin I

The Journal of Organic Chemistry ◽

10.1021/jo9001454 ◽

2009 ◽

Vol 74 (11) ◽

pp. 4080-4093 ◽

Cited By ~ 68

Author(s):

Clint A. James ◽

Victor Snieckus

Keyword(s):

Transition Metal ◽

Total Synthesis ◽

Cross Coupling ◽

Transition Metal Catalyzed ◽

Metal Catalyzed ◽

Coupling Strategies

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

Chemical Science ◽

10.1039/c8sc05502e ◽

2019 ◽

Vol 10 (10) ◽

pp. 3074-3079 ◽

Cited By ~ 9

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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