Total synthesis of pseudouridine via Heck-type C-glycosylation

2019 ◽  
Vol 43 (22) ◽  
pp. 8796-8803 ◽  
Author(s):  
Cheng-Ping Yu ◽  
Hsin-Yun Chang ◽  
Tun-Cheng Chien
Keyword(s):  
Total Synthesis ◽  
Functional Group ◽  
Type C

Pseudouridine (1) was synthesized by functional group interconversions of the Heck adduct 11 from 2,4-dimethoxy-5-iodopyrimidine (8) and ribofuranoid glycal 4.

scholarly journals Short, enantioselective, gram-scale synthesis of (−)-zephyranthine

2021 ◽  
Author(s):  
Yuxiang Zhao ◽  
Yanren Zhu ◽  
Guolan Ma ◽  
Qi Wei ◽  
Shaoxiong Yang ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Functional Group ◽  
Ring System ◽  
System Construction ◽  
Synthesis Design

A reasonable synthesis design by strategically integrating functional group manipulation into the ring system construction resulted in a short, enantioselective, gram-scale total synthesis of (−)-zephyranthine.

scholarly journals The Synthesis of Aigialomycin D Analogues

2021 ◽  
Author(s):  
◽  
Samuel Z.Y. Ting
Keyword(s):  
Total Synthesis ◽  
Functional Group ◽  
Biological Activities ◽  
Biological Testing ◽  
Hsp90 Inhibition ◽  
Vast Array ◽  
Synthetic Strategy ◽  
Structure Activity ◽  
Expansive Group ◽  
Resorcylic Acid Lactones

<p>Aigialomycin D is a fungal natural product possessing kinase inhibition properties. It is a member of a class of compounds known as the resorcylic acid lactones, a expansive group containing compounds exhibiting a vast array of biological activities. These include kinase and Hsp90 inhibition, highly desirable properties in the drug development field. This research project sought to capitalise on previous work involving the successful total synthesis of aigialomycin D. By developing the synthetic methodology, analogues of aigialomycin D could be prepared for biological testing to obtain valuable structure-activity relationship information. The focus of this thesis involves the successful synthesis of aigialomycin D diastereomer, 5',6'-epi,epi-aigialomycin D and the attempted synthesis of 100-epi-aigialomycin D, via the synthetic strategy developed previously in combination with enantiomeric starting material fragments ... The synthesis of functional group analogues, 6'-oxo-aigialomycin D, 7',8'-cyclopropyl aigialomycin D and 5-chloro-agialomycin D were also attempted via derivatisation of late-stage intermediates in the aigialomycin D synthesis. The thesis herein recounts the successes and failures in the synthesis of various aigialomycin D analogues ...</p>

Total Synthesis of Biselide A, A Cytotoxic Macrolide of Marine Origin

Synthesis ◽  
2017 ◽  
Vol 49 (13) ◽  
pp. 2958-2970 ◽  
Author(s):  
Ichiro Hayakawa ◽  
Hideo Kigoshi ◽  
Masami Okamura ◽  
Kazuaki Suzuki ◽  
Mami Shimanuki ◽  
...  
Keyword(s):  
Enzymatic Hydrolysis ◽  
Total Synthesis ◽  
Functional Group ◽  
Aldol Reaction ◽  
Oxygen Functional Group ◽  
Asymmetric Aldol ◽  
Marine Origin ◽  
Asymmetric Aldol Reaction ◽  
Cytotoxic Macrolide

The total synthesis of biselide A based on our earlier strategy of synthesizing haterumalides is reported. The highlights of this approach are the use of regioselective enzymatic hydrolysis for the installation of a C20 oxygen functional group and an asymmetric aldol reaction for the stereoselective introduction of a C3 oxygen functional group.

scholarly journals Catalyst-Controlled Regiodivergence in Rearrangements of Indole-Based Onium Ylides

2021 ◽  
Author(s):  
Vaishnavi Nair ◽  
Volga Kojasoy ◽  
Croix Laconsay ◽  
Dean Tantillo ◽  
Uttam Tambar
Keyword(s):  
Total Synthesis ◽  
Density Functional ◽  
Functional Group ◽  
Copper Catalyst ◽  
Indole Alkaloid ◽  
Functional Theory ◽  
Solvent Cage ◽  
Oxonium Ylides ◽  
Synthetic Intermediates

We have developed catalyst-controlled regiodivergent rearrangements of onium-ylides derived from indole substrates. Oxonium ylides formed <i>in situ</i> from substituted indoles selectively undergo [2,3]- and [1,2]-rearrangements in the presence of a rhodium and copper catalyst, respectively. The combined experimental and density functional theory (DFT) computational studies indicate divergent mechanistic pathways involving a metal-free ylide in the rhodium catalyzed reaction favoring [2,3]-rearrangement, and a metal-coordinated ion-pair in the copper catalyzed [1,2]-rearrangement that recombines in the solvent-cage. The application<br>of our methodology was demonstrated in the first total synthesis of the indole alkaloid (±)-sorazolon B, which enabled the stereochemical reassignment of the natural product. Further functional group transformations of the rearrangement products to generate valuable synthetic intermediates were also demonstrated.

Total Synthesis of Fargesine Using a Platinum-Catalyzed Intramolecular Friedel-Crafts-Type C–H Coupling–Allylic Amination Cascade

Heterocycles ◽  
2017 ◽  
Vol 95 (1) ◽  
pp. 243
Author(s):  
Tetsuhiro Nemoto ◽  
Yuito Tanaka ◽  
Yuta Suzuki ◽  
Yasumasa Hamada
Keyword(s):  
Total Synthesis ◽  
Allylic Amination ◽  
Type C

A synthesis of (+)-aphidicol-15-ene

1984 ◽  
Vol 62 (10) ◽  
pp. 1930-1932 ◽  
Author(s):  
Ronald B. Kelly ◽  
G. Sankar Lal ◽  
Gopala Gowda ◽  
Rabindra N. Rej
Keyword(s):  
Total Synthesis ◽  
Functional Group ◽  
Ring System ◽  
Stereospecific Synthesis

A stereospecific synthesis of (+)-aphidicol-15-ene is described. Pursuing a concept successfully applied to our total synthesis of stemarin and the stemodane diterpenoids, the C/D ring system was elaborated by functional group manipulation and rearrangement of a 6-hydroxybicyclo[2.2.2]octan-2-one system.

scholarly journals The Synthesis of Aigialomycin D Analogues

2021 ◽  
Author(s):  
◽  
Samuel Z.Y. Ting
Keyword(s):  
Total Synthesis ◽  
Functional Group ◽  
Biological Activities ◽  
Biological Testing ◽  
Hsp90 Inhibition ◽  
Vast Array ◽  
Synthetic Strategy ◽  
Structure Activity ◽  
Expansive Group ◽  
Resorcylic Acid Lactones

<p>Aigialomycin D is a fungal natural product possessing kinase inhibition properties. It is a member of a class of compounds known as the resorcylic acid lactones, a expansive group containing compounds exhibiting a vast array of biological activities. These include kinase and Hsp90 inhibition, highly desirable properties in the drug development field. This research project sought to capitalise on previous work involving the successful total synthesis of aigialomycin D. By developing the synthetic methodology, analogues of aigialomycin D could be prepared for biological testing to obtain valuable structure-activity relationship information. The focus of this thesis involves the successful synthesis of aigialomycin D diastereomer, 5',6'-epi,epi-aigialomycin D and the attempted synthesis of 100-epi-aigialomycin D, via the synthetic strategy developed previously in combination with enantiomeric starting material fragments ... The synthesis of functional group analogues, 6'-oxo-aigialomycin D, 7',8'-cyclopropyl aigialomycin D and 5-chloro-agialomycin D were also attempted via derivatisation of late-stage intermediates in the aigialomycin D synthesis. The thesis herein recounts the successes and failures in the synthesis of various aigialomycin D analogues ...</p>

A Concise Total Synthesis of (±)-Camptothecin

Synthesis ◽  
2019 ◽  
Vol 51 (18) ◽  
pp. 3506-3510
Author(s):  
Qian Liu ◽  
Guan-xin Huang ◽  
Min-jie Liu ◽  
Fen-Er Chen
Keyword(s):  
Total Synthesis ◽  
Michael Addition ◽  
Heck Reaction ◽  
Hydrobromic Acid ◽  
Functional Group ◽  
Domino Reaction ◽  
One Pot ◽  
Protective Groups ◽  
Efficient Scheme ◽  
Functional Group Transformation

A total synthesis of racemic camptothecin, characterized by a concise construction of the ring systems and easy functional group transformation, is described. A domino reaction consisting of a Heck reaction and an aza-intramolecular Michael addition to form the C ring serves as the first key step in the synthesis. The D ring was constructed by a simple Wittig–Horner reaction followed by removal of the protective groups. Hydroxymethylation, demethylation, and lactone formation reactions were performed in one-pot to construct the E ring under hydrobromic acid conditions. This work provides an efficient scheme for further synthetic exploration of camptothecin and its analogues.

scholarly journals A simple copper-catalyzed two-step one-pot synthesis of indolo[1,2-a]quinazoline

2014 ◽  
Vol 10 ◽  
pp. 2441-2447 ◽  
Author(s):  
Chunpu Li ◽  
Lei Zhang ◽  
Shuangjie Shu ◽  
Hong Liu
Keyword(s):  
Functional Group ◽  
One Pot ◽  
One Pot Synthesis ◽  
Type C ◽  
Quinazoline Derivatives

A convenient CuI/L-proline-catalyzed, two-step one-pot method has been developed for the preparation of indolo[1,2-a]quinazoline derivatives using a sequential Ullmann-type C–C and C–N coupling. This protocol provides an operationally simple and rapid strategy for preparing indolo[1,2-a]quinazoline derivatives and displays good functional group tolerance. All the starting materials are commercial available or can be easily prepared.

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