Synthesis via sigmatropic rearrangement. 12. Total synthesis of (+)-dihydrocostunolide via tandem Cope-Claisen rearrangement

1986 ◽  
Vol 51 (26) ◽  
pp. 5503-5505 ◽  
Author(s):  
Stanley Raucher ◽  
Ki Whan Chi ◽  
Ki Jun Hwang ◽  
John E. Burks
Keyword(s):  
Total Synthesis ◽  
Claisen Rearrangement ◽  
Sigmatropic Rearrangement

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 a protected form of sphingofungin E using the [3,3]-sigmatropic rearrangement of an allylic thiocyanate as the key reaction

2010 ◽  
Vol 345 (17) ◽  
pp. 2427-2437 ◽  
Author(s):  
Miroslava Martinková ◽  
Jozef Gonda ◽  
Jana Špaková Raschmanová ◽  
Michaela Slaninková ◽  
Juraj Kuchár
Keyword(s):  
Total Synthesis ◽  
Sigmatropic Rearrangement

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

Total synthesis of (±)-heliannuol C and E via aromatic Claisen rearrangement

2005 ◽  
Vol 46 (14) ◽  
pp. 2457-2460 ◽  
Author(s):  
James R. Vyvyan ◽  
Jennifer M. Oaksmith ◽  
Bevin W. Parks ◽  
Elaine M. Peterson
Keyword(s):  
Total Synthesis ◽  
Claisen Rearrangement ◽  
Aromatic Claisen Rearrangement

Total Synthesis of (±)-Cassumunins A–C and Curcumin Analogues

Synthesis ◽  
2020 ◽  
Vol 52 (10) ◽  
pp. 1561-1575 ◽  
Author(s):  
Faiz Ahmed Khan ◽  
Mulla Althafh Hussain
Keyword(s):  
Total Synthesis ◽  
Claisen Rearrangement ◽  
Aldol Condensation ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Full Account ◽  
Curcumin Analogues ◽  
Cross Coupling Reaction ◽  
Sigmatropic Shift ◽  
Novel Approaches

A full account of the total synthesis of (±)-cassumunins A–C – superior antioxidants and anti-inflammatory agents – is given. Two novel approaches were developed for synthesizing cassumunins. The total synthesis of cassumunins A and B was accomplished in five linear steps from a known aldehyde in good overall yields of 50 and 43%, respectively, featuring a cascade [3,3]-sigmatropic shift (the Claisen rearrangement) and Heck cross-coupling reaction. Consequently, the total synthesis of cassumunin C was accomplished in three linear steps from a known alcohol with an overall yield of 53%. The key features involved in this synthesis are tandem [3,3]-sigmatropic shift, SN2′ reaction, and aldol condensation. Moreover, a total of eighteen symmetrical and unsymmetrical curcumin analogues were synthesized.

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