Part I. A Scalable Synthesis of (−)-rasfonin Enabled by a Convergent Enantioselective [alpha]-hydroxymethylation Strategy PDF Download
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![Part I. A Scalable Synthesis of (−)-rasfonin Enabled by a Convergent Enantioselective [alpha]-hydroxymethylation Strategy PDF](https://books.google.com/books/content/images/frontcover/_3R1zQEACAAJ?fife=w150-h200)
Author: Justin Michael Niziol
Publisher:
ISBN:
Category :
Languages : en
Pages : 352
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Book Description
"Part I. A scalable synthesis of (-)-rasfonin enabled by a convergent enantioselective [alpha]-hydroxymethylation strategy. A scalable total synthesis of (-)-rasfonin, a potent antitumor agent, has been achieved. The synthetic strategy features a highly convergent approach based on a single protocol construction of both molecular hemispheres via catalytic enantioselective a-hydroxymethylation of simple aliphatic aldehydes. The described route has been successful in near-gram quantities of the natural product and serves as the first synthetic strategy to provide sufficient material for broad biological testing. With a keen focus on efficiency, atom economy, cost, and overall yield, the synthetic route described herein is certainly the shortest and most effective way currently described to synthesize significant quantities of (-)-rasfonin. Part II. Studies towards the total synthesis of FK-506. The synthesis of advanced intermediates towards the total synthesis of FK-506 is described herein. FK-506 has been an interesting synthetic target for some time, as it is not only structurally complex, but also a highly potent immunosuppressant. The purpose of the synthesis is to provide FK-506 in its natural form, as well as provide the option for late-stage functionalization in order to manipulate its level of toxicity. Our synthesis towards FK-506 is highly convergent, relying on the synthesis and combination of 4 subunits. Using a modified Julia olefination reaction, the major subunits of FK-506 have been successfully coupled to provide highly advanced structures. The following work also shows the improvement in yield, scalability, and simplicity of numerous reactions in the multiple routes towards the target molecule."--Pages ix-x.
![Part I. A Scalable Synthesis of (−)-rasfonin Enabled by a Convergent Enantioselective [alpha]-hydroxymethylation Strategy PDF](https://books.google.com/books/content/images/frontcover/_3R1zQEACAAJ?fife=w80-h100)
Author: Justin Michael Niziol
Publisher:
ISBN:
Category :
Languages : en
Pages : 352
Get Book Here
Book Description
"Part I. A scalable synthesis of (-)-rasfonin enabled by a convergent enantioselective [alpha]-hydroxymethylation strategy. A scalable total synthesis of (-)-rasfonin, a potent antitumor agent, has been achieved. The synthetic strategy features a highly convergent approach based on a single protocol construction of both molecular hemispheres via catalytic enantioselective a-hydroxymethylation of simple aliphatic aldehydes. The described route has been successful in near-gram quantities of the natural product and serves as the first synthetic strategy to provide sufficient material for broad biological testing. With a keen focus on efficiency, atom economy, cost, and overall yield, the synthetic route described herein is certainly the shortest and most effective way currently described to synthesize significant quantities of (-)-rasfonin. Part II. Studies towards the total synthesis of FK-506. The synthesis of advanced intermediates towards the total synthesis of FK-506 is described herein. FK-506 has been an interesting synthetic target for some time, as it is not only structurally complex, but also a highly potent immunosuppressant. The purpose of the synthesis is to provide FK-506 in its natural form, as well as provide the option for late-stage functionalization in order to manipulate its level of toxicity. Our synthesis towards FK-506 is highly convergent, relying on the synthesis and combination of 4 subunits. Using a modified Julia olefination reaction, the major subunits of FK-506 have been successfully coupled to provide highly advanced structures. The following work also shows the improvement in yield, scalability, and simplicity of numerous reactions in the multiple routes towards the target molecule."--Pages ix-x.
