scholarly journals Total Synthesis of Bryostatin 16 Using a Pd-Catalyzed Diyne Coupling as Macrocyclization Method and Synthesis of C20-epi-Bryostatin 7 as a Potent Anticancer Agent

2010 ◽  
Vol 132 (46) ◽  
pp. 16403-16416 ◽  
Author(s):  
Barry M. Trost ◽  
Guangbin Dong
Keyword(s):  
Total Synthesis ◽  
Anticancer Agent

Total Synthesis of Anticancer Agent EBC-23

2016 ◽  
Vol 18 (17) ◽  
pp. 4202-4205 ◽  
Author(s):  
Dodda Vasudeva Reddy ◽  
Gowravaram Sabitha ◽  
Tadikamalla Prabhakar Rao ◽  
Jhillu Singh Yadav
Keyword(s):  
Total Synthesis ◽  
Anticancer Agent

Towards a Total Synthesis of the New Anticancer Agent Mensacarcin: Synthesis of the Carbocyclic Core

2004 ◽  
Vol 10 (20) ◽  
pp. 5233-5242 ◽  
Author(s):  
Lutz F. Tietze ◽  
Scott G. Stewart ◽  
Marta E. Polomska ◽  
Andrea Modi ◽  
Axel Zeeck
Keyword(s):  
Total Synthesis ◽  
Anticancer Agent

A transition metal-free approach to a regioselective total synthesis of the natural product derivative 6-methylellipticine, a potent anticancer agent

2019 ◽  
Vol 60 (51) ◽  
pp. 151309 ◽  
Author(s):  
Song-Bo Lin ◽  
Wan-Wan Wang ◽  
Jin-Peng Meng ◽  
Xi-Wang Li ◽  
Jun Wu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Total Synthesis ◽  
Natural Product ◽  
Anticancer Agent ◽  
Metal Free

scholarly journals Paclitaxel as an anticancer agent: isolation, activity, synthesis and stability

Open Medicine ◽  
2011 ◽  
Vol 6 (5) ◽  
pp. 527-536 ◽  
Author(s):  
Vesna Nikolic ◽  
Ivan Savic ◽  
Ivana Savic ◽  
Ljubisa Nikolic ◽  
Mihajlo Stankovic ◽  
...  
Keyword(s):  
Chemical Modification ◽  
Total Synthesis ◽  
Anticancer Activity ◽  
Plant Material ◽  
Anticancer Agent ◽  
Aqueous Media ◽  
The Pacific ◽  
Other Substances ◽  
Synthesis Procedure ◽  
Isolated Compound

AbstractPaclitaxel is isolated from the Pacific yew. It can be obtained from the European yew, but only after chemical modification of the isolated compound by a semi-synthesis procedure. The procedure for total synthesis of paclitaxel is very complicated, involving multiple steps, and the yields of paclitaxel are meagre. This substance is also a metabolite of certain kinds of fungus. The microbiological pathway for producing paclitaxel compared with isolation from plant material involves shorter procuction times but a small yield. Cyclodextrins are usually used for improving the solubility of paclitaxel in aqueous media, with polymeric and other substances added. Paclitaxel has anticancer activity and use for preparing the formulations intravenously administrated to patients with tumors. The paclitaxel concentration in these formulations is determined using validated HPLC methods.

Total synthesis of the complex taxane diterpene canataxpropellane

Science ◽  
2020 ◽  
Vol 367 (6478) ◽  
pp. 676-681 ◽  
Author(s):  
Fabian Schneider ◽  
Konstantin Samarin ◽  
Simone Zanella ◽  
Tanja Gaich
Keyword(s):  
Total Synthesis ◽  
Anticancer Agent ◽  
Alder Reaction ◽  
Diels Alder ◽  
Core Structure ◽  
Natural Sources ◽  
The Core ◽  
Diels Alder Reaction ◽  
Cyclobutane Ring ◽  
Quaternary Carbons

Canataxpropellane belongs to the medicinally important taxane diterpene family. The most prominent congener, Taxol, is one of the most commonly used anticancer agent in clinics today. Canataxpropellane exhibits a taxane skeleton with three additional transannular C–C bonds, resulting in a total of six contiguous quaternary carbons, of which four are located on a cyclobutane ring. Unfortunately, isolation of canataxpropellane from natural sources is inefficient. Here, we report a total synthesis of (–)-canataxpropellane in 26 steps and 0.5% overall yield from a known intermediate corresponding to 29 steps from commercial material. The core structure of the (–)-canataxpropellane (2) was assembled in two steps using a Diels–Alder/ortho-alkene-arene photocycloaddition sequence. Enantioselectivity was introduced by designing chiral siloxanes to serve as auxiliaries in the Diels–Alder reaction.

The Trost Synthesis of Bryostatin 16

2013 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Natural Products ◽  
Transition Metal ◽  
Total Synthesis ◽  
Anticancer Agent ◽  
Selective Reduction ◽  
Unsaturated Aldehyde ◽  
Stanford University ◽  
Structure Activity ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

In a showcase for the specific transition metal–catalyzed couplings that he has developed, including the elegant Ru-catalyzed coupling of 1 and 2, Barry M. Trost of Stanford University reported (Nature 2008, 456, 485; J. Am. Chem. Soc. 2010, 132, 16403) the total synthesis of the potent anticancer agent, bryostatin 16 4. The preparation of 1 began with commercial 2,2-dimethylpropanediol 5. Brown allylation of the aldehyde 6 followed by protection and oxidative cleavage delivered 8. Condensation (J. Am. Chem. Soc. 2000, 122, 11727) with 9 followed by selective reduction and Sn-catalyzed lactonization led to 10, which was carried on to the ketone 1. The aldehyde 6 was also the starting material for the preparation of 2. Addition of the anion 12 followed by hydrolysis established the unsaturated aldehyde, which was combined with 13 to give the racemic alcohol 14. Oxidation followed by Itsuno-Corey reduction then completed the synthesis of 2. What followed was a spectacular sequence of three transition metal–catalyzed transformations. Intermolecular Ru-mediated coupling of 1 with 2 delivered the tetrahydropyran 3. Pd catalysis effected the selective intramolecular coupling of the two alkynes of the derived ester 15, to give 16. The constrained alkynyl alcohol 16 cyclized under Au catalysis to give the dihydropyran 17, completing the construction of the skeleton of bryostatin 16 4. The route to the bryostatins outlined here is short enough (26 linear steps) and flexible enough to allow a thorough search of structure–activity relationships for this potent class of natural products.

Two-Phase Synthesis of Taxol®

2020 ◽  
Author(s):  
Yuzuru Kanda ◽  
Hugh Nakamura ◽  
Shigenobu Umemiya ◽  
Ravi Kumar Puthukanoori ◽  
Venkata Ramana Murthy Appala ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Anticancer Agent ◽  
Synthetic Approach ◽  
Two Phase ◽  
Phase Synthesis ◽  
Natural Plant ◽  
Natural Isolates ◽  
Terpene Synthesis ◽  
The Subject ◽  
Biosynthetic Machinery

<p>Taxol® is widely regarded as amongst the most famed natural isolates ever discovered, and has been the subject of innumerable studies in both basic and applied science. Its documented success as an anticancer agent, coupled with early concerns over supply, stimulated a furious worldwide effort from chemists to provide a solution for its preparation through total synthesis. Those pioneering studies proved the feasibility of retrosynthetically-guided access to synthetic Taxol, albeit in minute quantities and with enormous effort. In practice, all medicinal chemistry efforts and eventual commercialization have relied upon natural- (plant</p> <p>material) or biosynthetically-derived (synthetic biology) supplies. Here we show how a complementary divergent synthetic approach that is holistically patterned off of biosynthetic machinery for terpene synthesis can be used to arrive at Taxol®.</p>

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