scholarly journals A Concise and Efficient Total Synthesis of α-Mangostin and β-Mangostin from Garcinia Mangostana

2013 ◽  
Vol 8 (8) ◽  
pp. 1934578X1300800
Author(s):  
Dandan Xu ◽  
Ying Nie ◽  
Xizhou Liang ◽  
Ling Ji ◽  
Songyuan Hu ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Wittig Reaction ◽  
Claisen Rearrangement ◽  
Practical Approach ◽  
Efficient Synthesis ◽  
Garcinia Mangostana ◽  
Diverse Groups

The concise, efficient synthesis of α-mangostin is described in eight simple steps with 8.3% overall yield. Highlights include a practical approach to construct the isopentene groups and other diverse groups at C–2 and C–8 of the xanthene skeleton through Claisen rearrangement and Wittig reaction. Meanwhile the first total synthesis of β-mangostin is presented with a similar approach.

Total Synthesis of Icaritin via Microwave-assistance Claisen Rearrangement

2014 ◽  
Vol 11 (9) ◽  
pp. 677-681 ◽  
Author(s):  
Van-Son Nguyen ◽  
Ling Shi ◽  
Yue Li ◽  
Qiu-An Wang
Keyword(s):  
Total Synthesis ◽  
Claisen Rearrangement ◽  
Microwave Assistance

Total Synthesis of S-(+)-Argentilactone

2001 ◽  
Vol 56 (3) ◽  
pp. 325-328 ◽  
Author(s):  
Muhammad Saeed ◽  
Muhammad Abbas ◽  
Khalid Mohammad Khan ◽  
Wolfgang Voelter
Keyword(s):  
Total Synthesis ◽  
Wittig Reaction ◽  
Subsequent Oxidation

Abstract Asymmetrie Total Synthesis Asymmetrie total synthesis of S-(+)-argentilactone (2) was accomplished, using methyl-a-D-glucopyranoside (3) as carbohydrate template. Benzylidene acetal 5 was hydrolysed with tBuOOH/AlCl3 and further manipulated to produce the aldehyde 10. A Wittig reaction and subsequent oxidation of the anomeric position yielded the target argentilactone.

Synthetic Approaches Towards the Total synthesis of tubulysin and its fragments: A review

2021 ◽  
Vol 19 ◽  
Author(s):  
Nosheen Iqbal ◽  
Ameer Fawad Zahoor ◽  
Nasir Rasool ◽  
Samreen Gul Khan ◽  
Rabia Akhtar ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Claisen Rearrangement ◽  
Antitumor Agents ◽  
Aldol Reaction ◽  
Multidrug Resistant ◽  
Novel Drugs ◽  
Mukaiyama Aldol ◽  
Ic50 Values ◽  
Barbier Reaction ◽  
Synthetic Approaches

Background: Tubulysins, linear tetrapeptides show extraordinary cytotoxicity against various cancer cells, with IC50 values in nano or picomolar range. Due to their extremely vigorous anti-proliferative and antiangiogenic characteristics, tubulysins exhibit captivating prospects in the development of anticancer drugs. This review focuses on diverse routes for the total synthesis of natural and synthetic tubulysins as well as their fragments. Objective: The purpose of this review is to present the synthetic strategies for the development of antitumor agents, tubulysins. Conclusion: A range of synthetic pathways adopted for the total synthesis of tubulysins and their fragments have been described in this review. Synthesis of fragments, Tuv, Tup, and Tut can be accomplished by adopting appropriate strategies such as Manganese-mediated synthesis, Ireland-Claisen rearrangement, Mukaiyama aldol reaction, and Mannich process etc. Tubulysin B, D, U, V, and N14-desacetoxytubulysin H have been prepared through Mitsunobu reaction, tert-butanesulfinamide method, Tandem reaction, aza-Barbier reaction, Evans aldol reaction, and C-H activation strategies etc. The remarkable anticancer potential of tubulysins toward a substantiate target make them prominent leads for developing novel drugs against multidrug-resistant cancers.

A Concise Total Synthesis of (±)-Mesembrine

Synlett ◽  
2018 ◽  
Vol 29 (09) ◽  
pp. 1203-1206 ◽  
Author(s):  
Hyoungsu Kim ◽  
Hosam Choi ◽  
Kiyoun Lee
Keyword(s):  
Total Synthesis ◽  
Claisen Rearrangement ◽  
Addition Reaction ◽  
Conjugate Addition ◽  
Allylic Oxidation ◽  
Quaternary Stereocenter

A concise total synthesis of (±)-mesembrine has been successfully accomplished in seven steps and 24% overall yield from commercially available 3-ethoxy-2-cyclohexen-1-one. Central to the assembly of the skeleton of mesembrine are a Johnson–Claisen rearrangement for the formation of the benzylic quaternary stereocenter and direct allylic oxidation to generate the substrate for the amidation/transannular aza-conjugate addition reaction.

ChemInform Abstract: Total Synthesis of (-)-Flustramine B via One-Pot Intramolecular Ullmann Coupling and Claisen Rearrangement.

ChemInform ◽  
2009 ◽  
Vol 40 (41) ◽  
Author(s):  
Tomohiro Hirano ◽  
Kanako Iwakiri ◽  
Hiroshi Miyamoto ◽  
Atsuo Nakazaki ◽  
Susumu Kobayashi
Keyword(s):  
Total Synthesis ◽  
Claisen Rearrangement ◽  
One Pot ◽  
Ullmann Coupling
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