A Formal Total Synthesis of the ACE Inhibitor K-13. An Application of Arene-Ruthenium Chemistry to Complex Chemical Synthesis

1994 ◽  
Vol 59 (9) ◽  
pp. 2304-2313 ◽  
Author(s):  
Anthony J. Pearson ◽  
Kieseung Lee
Keyword(s):  
Chemical Synthesis ◽  
Total Synthesis ◽  
Ace Inhibitor ◽  
Complex Chemical ◽  
K 13

Computationally Augmented Retrosynthesis: Total Synthesis of Paspaline A and Emindole PB

2018 ◽  
Author(s):  
Timothy Newhouse ◽  
Daria E. Kim ◽  
Joshua E. Zweig
Keyword(s):  
Chemical Synthesis ◽  
Total Synthesis ◽  
Small Molecules ◽  
First Principles ◽  
Quantum Chemical ◽  
Computational Analysis ◽  
Empirical Evaluation ◽  
Synthetic Strategy ◽  
Catalyzed Reactions ◽  
Enzyme Catalyzed Reactions

The diverse molecular architectures of terpene natural products are assembled by exquisite enzyme-catalyzed reactions. Successful recapitulation of these transformations using chemical synthesis is hard to predict from first principles and therefore challenging to execute. A means of evaluating the feasibility of such chemical reactions would greatly enable the development of concise syntheses of complex small molecules. Herein, we report the computational analysis of the energetic favorability of a key bio-inspired transformation, which we use to inform our synthetic strategy. This approach was applied to synthesize two constituents of the historically challenging indole diterpenoid class, resulting in a concise route to (–)-paspaline A in 9 steps from commercially available materials and the first pathway to and structural confirmation of emindole PB in 13 steps. This work highlights how traditional retrosynthetic design can be augmented with quantum chemical calculations to reveal energetically feasible synthetic disconnections, minimizing time-consuming and expensive empirical evaluation.

Probing the SAR of dEpoB via Chemical Synthesis:  A Total Synthesis Evaluation of C26-(1,3-dioxolanyl)-12,13-desoxyepothilone B

2002 ◽  
Vol 67 (22) ◽  
pp. 7730-7736 ◽  
Author(s):  
Mark D. Chappell ◽  
Christina R. Harris ◽  
Scott D. Kuduk ◽  
Aaron Balog ◽  
Zhicai Wu ◽  
...  
Keyword(s):  
Chemical Synthesis ◽  
Total Synthesis

scholarly journals Efficiency Eff syn of complex syntheses as multicomponent reactions, its algorithm and calculations based on concrete criteria

2019 ◽  
Vol 15 ◽  
pp. 1425-1433
Author(s):  
Heiner Eckert
Keyword(s):  
Green Chemistry ◽  
Chemical Synthesis ◽  
Data Processing ◽  
Multicomponent Reactions ◽  
Cost Assessment ◽  
Complex Chemical ◽  
Economic Progress ◽  
Strict Compliance ◽  
And Control ◽  
Mathematical Operations

A synthesis efficiency algorithm, which must be based on concrete and reliable criteria, is essential for the evaluation and control of complex chemical synthesis, notably multicomponent reactions (MCRs). An algorithm has been developed to precisely evaluate even highly complex syntheses with regards to their synthesis efficiency Eff syn as a tool for strict compliance with green chemistry requirements, and for economic progress. The mathematical operations are highly suitable for electronic data processing (EDP). This algorithm is also suitable as a basis for fair cost assessment of complex chemical syntheses.

scholarly journals Linear Triquinane Sesquiterpenoids: Their Isolation, Structures, Biological Activities, and Chemical Synthesis

Molecules ◽  
2018 ◽  
Vol 23 (9) ◽  
pp. 2095 ◽  
Author(s):  
Yi Qiu ◽  
Wen-Jian Lan ◽  
Hou-Jin Li ◽  
Liu-Ping Chen
Keyword(s):  
Chemical Synthesis ◽  
Total Synthesis ◽  
Chemical Structure ◽  
Biological Activities ◽  
Structural Diversity ◽  
Structure Identification ◽  
Important Class ◽  
Soft Corals ◽  
Wide Range ◽  
New Challenges

Linear triquinane sesquiterpenoids represent an important class of natural products. Most of these compounds were isolated from fungi, sponges, and soft corals, and many of them displayed a wide range of biological activities. On account of their structural diversity and complexity, linear triquinane sesquiterpenoids present new challenges for chemical structure identification and total synthesis. 118 linear triquinane sesquiterpenoids were classified into 8 types, named types I–VIII, based on the carbon skeleton and the position of carbon substituents. Their isolation, structure elucidations, biological activities, and chemical synthesis were reviewed. This paper cited 102 articles from 1947 to 2018.

ChemInform Abstract: An Efficient Total Synthesis of K-13, a Non-Competitive Inhibitor of ACE I.

ChemInform ◽  
2010 ◽  
Vol 31 (36) ◽  
pp. no-no
Author(s):  
Antony Bigot ◽  
Michele Bois-Choussy ◽  
Jieping Zhu
Keyword(s):  
Total Synthesis ◽  
Competitive Inhibitor ◽  
K 13
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