ChemInform Abstract: Protecting-Group-Free Total Synthesis of (-)-Rhazinilam (VII) and (-)-Rhazinicine (VIII) Using a Gold-Catalyzed Cascade Cyclization.

ChemInform ◽  
2013 ◽  
Vol 44 (48) ◽  
pp. no-no
Author(s):  
Kenji Sugimoto ◽  
Kazuki Toyohima ◽  
Shiori Nonaka ◽  
Kenta Kotaki ◽  
Hirofumi Ueda ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Protecting Group ◽  
Cascade Cyclization

Protecting-Group-Free Total Synthesis of (−)-Rhazinilam and (−)-Rhazinicine using a Gold-Catalyzed Cascade Cyclization

2013 ◽  
Vol 52 (28) ◽  
pp. 7168-7171 ◽  
Author(s):  
Kenji Sugimoto ◽  
Kazuki Toyoshima ◽  
Shiori Nonaka ◽  
Kenta Kotaki ◽  
Hirofumi Ueda ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Protecting Group ◽  
Cascade Cyclization

Protecting-Group-Free Total Synthesis of (−)-Rhazinilam and (−)-Rhazinicine using a Gold-Catalyzed Cascade Cyclization

2013 ◽  
Vol 125 (28) ◽  
pp. 7309-7312 ◽  
Author(s):  
Kenji Sugimoto ◽  
Kazuki Toyoshima ◽  
Shiori Nonaka ◽  
Kenta Kotaki ◽  
Hirofumi Ueda ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Protecting Group ◽  
Cascade Cyclization

Short Protecting Group-free Syntheses of CDE Synthon of Racemic Camptothecin

2020 ◽  
Vol 17 (7) ◽  
pp. 588-591
Author(s):  
Pingxuan Shao ◽  
Wei Lu ◽  
Lei Wang
Keyword(s):  
Total Synthesis ◽  
Future Development ◽  
Protecting Group ◽  
Short Route ◽  
The Future ◽  
Tricyclic Ketone

A practical and concise total synthesis of tricyclic ketone 7 (CDE ring), a valuable intermediate for the synthesis of racemic camptothecin and analogs, was described (8 chemical steps and 29% overall yield). The synthesis starts with two inexpensive, readily available materials and is operationally simple to perform. It is worth mentioning that the reported protecting group-free synthesis, with advantages of a short route, would be helpful for the future development of industry-scale syntheses of camptothecin-family alkaloids.

Concise asymmetric total synthesis of lycopodine and flabelliformine via cascade cyclization reaction

2019 ◽  
Vol 60 (2) ◽  
pp. 187-190 ◽  
Author(s):  
Kentaro Wada ◽  
Noriyuki Kogure ◽  
Mariko Kitajima ◽  
Hiromitsu Takayama
Keyword(s):  
Total Synthesis ◽  
Cyclization Reaction ◽  
Asymmetric Total Synthesis ◽  
Cascade Cyclization

Asymmetric total synthesis of cryptoconcatone I

2019 ◽  
Vol 17 (14) ◽  
pp. 3552-3566 ◽  
Author(s):  
Ranjan Kumar Acharyya ◽  
Pratik Pal ◽  
Shrestha Chatterjee ◽  
Samik Nanda
Keyword(s):  
Total Synthesis ◽  
Late Stage ◽  
Ring Opening ◽  
Epoxide Ring ◽  
Asymmetric Total Synthesis ◽  
Epoxide Ring Opening ◽  
Cascade Cyclization ◽  
Naturally Occurring

An efficient asymmetric total synthesis of naturally occurring γ-Z-butenolide cryptoconcatone I was achieved by employing substrate-directed reductive epoxide ring opening and late-stage “Pd–Cu” catalyzed cascade cyclization.

scholarly journals Revision of the Structure and Total Synthesis of Topsentin C

Synthesis ◽  
2017 ◽  
Vol 49 (11) ◽  
pp. 2562-2574 ◽  
Author(s):  
Nikita Golantsov ◽  
Alexey Festa ◽  
Alexey Varlamov ◽  
Leonid Voskressensky
Keyword(s):  
Total Synthesis ◽  
Secondary Metabolite ◽  
Conjugate Addition ◽  
Solvent Free ◽  
Synthetic Approach ◽  
Protecting Group ◽  
Marine Alkaloids ◽  
Mild Reduction

An efficient synthetic approach to access (indol-3-yl)ethane-1,2-diamines with a protecting group at the indole N atom from readily available 3-(2-nitrovinyl)indoles is reported. This approach includes solvent-free conjugate addition of O-pivaloylhydroxylamines to 1-Boc-3-(2-nitrovinyl)indoles followed by mild reduction of the adducts. The obtained (indol-3-yl)ethane-1,2-diamines are convenient synthetic precursors for several classes of marine alkaloids. The first total synthesis of racemic topsentin C, a secondary metabolite from Hexadella sp., based on this approach is reported. The initially proposed structure for topsentin C has been revised.

scholarly journals A Reliable Enantioselective Route to Mono-Protected N1-Cbz Piperazic Acid Building Block

Molecules ◽  
2020 ◽  
Vol 25 (24) ◽  
pp. 5939
Author(s):  
Evanthia Papadaki ◽  
Dimitris Georgiadis ◽  
Michail Tsakos
Keyword(s):  
Natural Products ◽  
Amino Acid ◽  
Total Synthesis ◽  
Building Block ◽  
Optical Purity ◽  
Protecting Group ◽  
High Optical Purity

The chiral N1-Cbz, N2-H derivative of the piperazic acid monomer is a valuable building block in the total synthesis of natural products, comprising this nonproteinogenic amino acid. In that context, we wish to report an improved synthetic protocol for the synthesis of both (3R)- and (3S)-piperazic acids bearing the carboxybenzyl protecting group (Cbz) selectively at the N1 position. Our method builds on previously reported protocols, circumventing their potential shortcomings, and optimizing the ultimate selective deprotection at the N2 position, thus, offering an efficient and reproducible pathway to suitably modified piperazates in high optical purity.

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