Total Synthesis of (−)-Calycanthine via Iron-Catalyzed Stereoselective Oxidative Dimerization

2021 ◽  
Author(s):  
Leiyang Bai ◽  
Yinhao Ma ◽  
Xuefeng Jiang
Keyword(s):  
Total Synthesis ◽  
Oxidative Dimerization

Oxidative Electro-organic Synthesis of Dimeric Hexahydropyrrolo-[2,3-b]indole Alkaloids Involving PCET: Total Synthesis of (±)-Folicanthine

2021 ◽  
Author(s):  
Kundan Shaw ◽  
Sulekha Sharma ◽  
Arindam Khatua ◽  
Amit Paul ◽  
Alakesh Bisai
Keyword(s):  
Total Synthesis ◽  
Organic Synthesis ◽  
Indole Alkaloids ◽  
Oxidative Dimerization

An efficient electrochemical strategy has been developed for the total synthesis of dimeric hexahydropyrrolo[2,3-b]indole alkaloids. In particular, oxidative dimerization of 3-alkyl 2-oxindoles was developed for this study. A detailed CV...

Oxidative dimerization of Nb-acyltryptophans total synthesis and absolute configuration of ditryptophenaline

1981 ◽  
Vol 22 (52) ◽  
pp. 5323-5326 ◽  
Author(s):  
Masako Nakagawa ◽  
Hiroyuki Sugumi ◽  
Shinichi Kodato ◽  
Tohru Hino
Keyword(s):  
Total Synthesis ◽  
Absolute Configuration ◽  
Oxidative Dimerization

‘Biomimetic’ oxidative dimerization of korupensamine A: Completion of the first total synthesis of michellamines A, B, and C

Tetrahedron ◽  
1994 ◽  
Vol 50 (32) ◽  
pp. 9643-9648 ◽  
Author(s):  
Gerhard Bringmann ◽  
Sven Harmsen ◽  
Jörg Holenz ◽  
Torsten Geuder ◽  
Roland Götz ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Oxidative Dimerization

Oxidative Dimerization of 2-Oxindoles Promoted by KOtBu-I2: Total Synthesis of (±)-Folicanthine

2015 ◽  
Vol 17 (6) ◽  
pp. 1373-1376 ◽  
Author(s):  
Santanu Ghosh ◽  
Saikat Chaudhuri ◽  
Alakesh Bisai
Keyword(s):  
Total Synthesis ◽  
Oxidative Dimerization

scholarly journals Unprecedented and Scalable Copper (I)-Catalyzed Oxidation of the Csp2-H bond on 2-phenyl-naphthalene-1,3-diol with Atmospheric Oxygen: synthesis of 2-Hydroxy-3-phenyl-1,4-naphthoquinone via direct Csp2-O bond formation

2017 ◽  
Vol 27 (5) ◽  
pp. 62-68 ◽  
Author(s):  
Sheila Teresita Guardado-Cruz ◽  
Rafael Ortiz-Alvarado ◽  
Claudia De León ◽  
César Rogelio Solorio-Alvarado
Keyword(s):  
Total Synthesis ◽  
Atmospheric Oxygen ◽  
Bond Formation ◽  
Hypervalent Iodine ◽  
Direct Oxidation ◽  
Oxidative Dimerization ◽  
Reaction Conditions ◽  
Oxidation Processes ◽  
Dimerization Product ◽  
Catalyzed Oxidation

The Csp2-O bond formation via direct oxidation of the Csp2-H bond on electron-rich compounds such as naphthols, is a process that generally requires drastic reaction conditions like high temperature or pressure. Addition of strong oxidants as H2O2, hypervalent iodine reagents (λ3 o λ5), expensive transition metals or rare earth elements, such as Mo, Ru Pt or Ce, is usually necessary. As part of this study on oxidative dimerization of phenols towards the total synthesis of ningalin D, 1,3-naphthalenediol was explored as starting material using stoichiometric amounts of Cu(I) and atmospheric molecular oxygen. A novel two-step sequence reaction for the formation of a 1,4-naphthoquinone was found instead of a dimerization product. The synthesis of this compound involves two consecutive oxidation processes. 

scholarly journals Total Synthesis of Hybocarpone, a Cytotoxic Naphthazarin Derivative from the Lichen Lecanora hybocarpa, and Related Compounds

2014 ◽  
Vol 9 (12) ◽  
pp. 1934578X1400901 ◽  
Author(s):  
Sergey V. Dragan ◽  
Michael A. Pushilin ◽  
Valery P. Glazunov ◽  
Vladimir A. Denisenko ◽  
Victor Ph. Anufriev
Keyword(s):  
Total Synthesis ◽  
Antitumor Agent ◽  
Synthetic Approach ◽  
Oxidative Dimerization ◽  
Carbon Carbon Bonds ◽  
Carbon Bonds ◽  
Related Compounds

The concise synthesis of the lichen-derived antitumor agent hybocarpone (1) and its analogs is described. A new synthetic approach is based on the direct oxidative dimerization of the available naphthazarin precursors in the formation of the binaphtho[2,3- b; 2,3- d]furantetraone structure. It was shown that the first step to tetrahydrofuran features is the bridging hindered S*, S* and R*, S* carbon-carbon bonds of the molecules, setting the relative configurations of the 5a S*,6a S*,12a S*,12b S* and 5a S*,6a R*,12a R*,12b S* diastereomers.

Biomimetic Total Synthesis of Scabellone B

Synlett ◽  
2018 ◽  
Vol 29 (12) ◽  
pp. 1617-1621 ◽  
Author(s):  
Xiangdong Hu ◽  
Tao Yu ◽  
Xin Shu ◽  
Kewu Yang
Keyword(s):  
Total Synthesis ◽  
Oxidative Dimerization ◽  
Biomimetic Approach

A biomimetic total synthesis of scabellone B is described. Through sequential regioselective introduction of a geranyl group by means of silyl protection, oxidative dimerization, and biomimetic oxo-6π electrocyclization with good cyclization selectivity, a biomimetic ­approach to scabellone B was achieved in five steps and 32% overall yield.

Sign in / Sign up

Export Citation Format

Share Document