Large-Scale Enantioselective Preparation of 2E,7E, 5S,6R, 5-Hydroxy-6-methyl-8-phenyl-octa-2,7-dienoic Acid, a Key Fragment for the Formal Total Synthesis of the Anti-tumor Agent Cryptophycin 52

2006 ◽  
pp. 37-51
Author(s):  
James Aikins ◽  
Tony Y. Zhang ◽  
Milton Zmijewski ◽  
Barbara Briggs
Keyword(s):  
Total Synthesis ◽  
Large Scale ◽  
Dienoic Acid ◽  
Cryptophycin 52 ◽  
Tumor Agent

Radiosynthesis of a Novel PET Fluoronicotinamide for Melanoma Tumour PET Imaging; [18F]MEL050

2011 ◽  
Vol 64 (7) ◽  
pp. 873 ◽  
Author(s):  
Ivan Greguric ◽  
Stephen Taylor ◽  
Tien Pham ◽  
Naomi Wyatt ◽  
Cathy D. Jiang ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Large Scale ◽  
Radiochemical Purity ◽  
Specific Activity ◽  
Phase 1 ◽  
Radiochemical Yield ◽  
Synthesis Time ◽  
Clinical Phase ◽  
One Step ◽  
No Carrier Added

[18F]6-Fluoro-N-[2-(diethylamino)ethyl]nicotinamide [18F]MEL050 is a novel nicotinamide-based radiotracer, designed to target random metastatic dissemination of melanoma tumours by targeting melanin. Preclinical studies suggest that [18F]MEL050 has an excellent potential to improve diagnosis and staging of melanoma. Here we report the radiochemical optimization conditions of [18F]MEL050 and its large scale automated synthesis using a GE FXFN automated radiosynthesis module for clinical, phase-1 investigation. [18F]MEL050 was prepared via a one-step synthesis using no-carrier added K[18F]F-Krytpofix® 222 (DMSO, 170°C, 5 min) followed by HPLC purification. Using 6-chloro-N-[2-(diethylamino)ethyl]nicotinamide as precursor, [18F]MEL050 was obtained in 40–46% radiochemical yield (non-decay corrected), in greater than 99.9% radiochemical purity and specific activity ranging from 240 to 325 GBq μmol–1. Total synthesis time including formulation was 40 min and [18F]MEL050 was stable (99.8%) in PBS for 6 h.

scholarly journals Total Synthesis of Mycalisine B

Marine Drugs ◽  
2019 ◽  
Vol 17 (4) ◽  
pp. 226 ◽  
Author(s):  
Haixin Ding ◽  
Zhizhong Ruan ◽  
Peihao Kou ◽  
Xiangyou Dong ◽  
Jiang Bai ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Large Scale ◽  
Reaction Conditions ◽  
Naturally Occurring ◽  
Key Steps

The first total synthesis of the marine nucleoside Mycalisine B—a naturally occurring and structurally distinct 4,5-unsaturated 7-deazapurine nucleoside—has been accomplished in 10 linear steps with 27.5% overall yield from commercially available 1,2,3,5-tetra-O-acetyl-ribose and tetracyanoethylene. Key steps of the approach include: (1) I2 catalyzed acetonide formation from 1,2,3,5-tetra-O-acetylribose and acetone at large scale; (2) Vorbrüggen glycosylation using N4-benzoyl-5-cyano-6-bromo-7H-pyrrolo[2,3–d]pyrimidine as a nucleobase to avoid formation of N-3 isomer; (3) mild and scalable reaction conditions.

scholarly journals Efficient and Reproducible Synthesis of an Fmoc-protected Tn Antigen

2021 ◽  
Author(s):  
Michael R. Reynolds ◽  
Sabrina Piazza ◽  
Jonathan Chiaramonte ◽  
Fabiola A. Chapa-Villarreal ◽  
John Trant
Keyword(s):  
Total Synthesis ◽  
Peptide Synthesis ◽  
Building Block ◽  
Large Scale ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Tn Antigen ◽  
Palladium Catalyzed ◽  
Glycosyl Donor ◽  
Antigen A

The total synthesis of the Thomsen-nouveau (Tn) antigen, a tumour-associated O-linked mucin glycopeptide, was achieved through a concise route. The key glycosylation step proved challenging to reproduce from the literature precedents and was most reliably accomplished using a palladium-catalyzed coupling between the glycosyl donor and Fmoc-functionalized serine acceptor to form the target in moderate yields. This is, to the best of our knowledge, the shortest synthesis reported from galactose for preparing this essential building block for large-scale solid phase peptide synthesis.

scholarly journals The First Total Synthesis of (±)-Methyl Salvianolate A Using a Convergent Strategy

Molecules ◽  
2019 ◽  
Vol 24 (5) ◽  
pp. 999
Author(s):  
Bo Wang ◽  
Liping Wang ◽  
Ying Peng ◽  
Yiying Pang ◽  
Hesheng Xiao ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Large Scale ◽  
Protecting Groups ◽  
Key Features

Herein, a convergent, practicable and first total synthesis of the natural product, (±)-methyl salvianolate A, is reported. The key features of the approach are the use of a Horner–Wadsworth–Emmons reaction and the protection of multiple hydroxyls using silyl protecting groups. The employment of the readily removable silyl protecting groups allows the synthesis of (±)-methyl salvianolate A and its derivatives on a reasonably large scale.

Highly-Efficient Preparation of Key Intermediate of Huperzine A

2014 ◽  
Vol 484-485 ◽  
pp. 157-160
Author(s):  
Kai Ming Xie
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Potential Application ◽  
Large Scale ◽  
Huperzine A ◽  
Synthetic Route ◽  
Alzheimers Disease ◽  
Highly Efficient ◽  
Large Scale Preparation ◽  
Scale Preparation

Huperzine A was approved for curing Alzheimers disease in the early 1990s in China. We explored a highly-efficient synthetic route for the key intermediate in the total synthesis of this natural product. Only common reagents and conditions were involved. So our new route has potential application in large-scale preparation of the key intermediate.

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