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.

scholarly journals Total synthesis of the proposed structure of astakolactin

2014 ◽  
Vol 10 ◽  
pp. 2421-2427 ◽  
Author(s):  
Takayuki Tonoi ◽  
Keisuke Mameda ◽  
Moe Fujishiro ◽  
Yutaka Yoshinaga ◽  
Isamu Shiina
Keyword(s):  
Total Synthesis ◽  
Marine Sponge ◽  
Claisen Rearrangement ◽  
Aldol Reaction ◽  
Mukaiyama Aldol Reaction ◽  
Mukaiyama Aldol

The first total synthesis of the proposed structure of astakolactin, a sesterterpene metabolite isolated from the marine sponge Cacospongia scalaris, has been achieved, mainly featuring Johnson–Claisen rearrangement, asymmetric Mukaiyama aldol reaction and MNBA-mediated lactonization.

An efficient catalyst-free Mukaiyama-aldol reaction of fluorinated enol silyl ethers with tryptanthrin

2015 ◽  
Vol 13 (33) ◽  
pp. 8906-8911 ◽  
Author(s):  
Fu-Min Liao ◽  
Yun-Lin Liu ◽  
Jin-Sheng Yu ◽  
Feng Zhou ◽  
Jian Zhou
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Aldol Reaction ◽  
Efficient Catalyst ◽  
Silyl Ethers ◽  
Mukaiyama Aldol Reaction ◽  
Catalyst Free ◽  
Mukaiyama Aldol ◽  
Enol Silyl Ethers ◽  
Fluoroalkyl Group

We report an efficient Mukaiyama-aldol reaction of tryptanthrin with fluorinated enol silyl ethers, which is carried out in methanol without the use of any catalyst. This represents the first modification of tryptanthrin by a fluoroalkyl group, which is applied to the total synthesis of the difluoro analogues of the natural product Phaitanthrin B.

Total Synthesis of Khafrefungin Using Highly Stereoselective Vinylogous Mukaiyama Aldol Reaction

2007 ◽  
Vol 9 (5) ◽  
pp. 849-852 ◽  
Author(s):  
Shin-ichi Shirokawa ◽  
Mariko Shinoyama ◽  
Isao Ooi ◽  
Seijiro Hosokawa ◽  
Atsuo Nakazaki ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Aldol Reaction ◽  
Mukaiyama Aldol Reaction ◽  
Mukaiyama Aldol

The Impact of the Mukaiyama Aldol Reaction in Total Synthesis

2013 ◽  
Vol 52 (35) ◽  
pp. 9097-9108 ◽  
Author(s):  
S. B. Jennifer Kan ◽  
Kenneth K.-H. Ng ◽  
Ian Paterson
Keyword(s):  
Total Synthesis ◽  
Aldol Reaction ◽  
Mukaiyama Aldol Reaction ◽  
Mukaiyama Aldol ◽  
The Impact

scholarly journals Optimization of Two Steps in Scale-Up Synthesis of Nannocystin A

Marine Drugs ◽  
2021 ◽  
Vol 19 (4) ◽  
pp. 198
Author(s):  
Tingrong Zhang ◽  
Shaojie Miao ◽  
Mingxiao Zhang ◽  
Wenjie Liu ◽  
Liang Wang ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Aldol Reaction ◽  
Scale Up ◽  
Scaling Up ◽  
Mukaiyama Aldol Reaction ◽  
Mukaiyama Aldol ◽  
Cost Efficient

We have accomplished a 10-step (longest linear) total synthesis of nannocystin A on a four hundred milligram scale. The previously reported Kobayashi vinylogous Mukaiyama aldol reaction to connect C4 and C5 was unreproducible during the scaling up process. A more convenient and cost-efficient Keck asymmetric vinylogous aldol reaction was employed to improve this transformation.

scholarly journals Total Synthesis of Khafrefungin Using Highly Stereoselective Vinylogous Mukaiyama Aldol Reaction.

ChemInform ◽  
2007 ◽  
Vol 38 (30) ◽  
Author(s):  
Shin-ichi Shirokawa ◽  
Mariko Shinoyama ◽  
Isao Ooi ◽  
Seijiro Hosokawa ◽  
Atsuo Nakazaki ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Aldol Reaction ◽  
Mukaiyama Aldol Reaction ◽  
Mukaiyama Aldol

A Diamino Alcohol Catalyzed Enantioselective Crossed Aldol Reaction of Acetaldehyde with Isatins - A Concise Total Synthesis of Antitumor Agents

2017 ◽  
Vol 2017 (26) ◽  
pp. 3874-3885 ◽  
Author(s):  
Ummareddy Venkata Subba Reddy ◽  
Madhu Chennapuram ◽  
Kento Seki ◽  
Chigusa Seki ◽  
Bheemreddy Anusha ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Antitumor Agents ◽  
Aldol Reaction
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