Computer-Assisted Design of Complex Organic Syntheses

Corey, E. J.; Wipke, W. Todd

doi:10.1126/science.166.3902.178

Cited by 587 publications

(370 citation statements)

References 26 publications

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“…18 The existence of simple yet predictive "arrow pushing" heuristics for polar organic reactions strongly indicates that a useful heuristic scheme may be developed from these rules. Rule-based systems have been successfully used for development and optimization of organic syntheses since the pioneering work of Corey and Wipke over 40 years ago 11,[19][20][21][22][23][24][25] and have been recently developed into a broad-spectrum synthetic tool by Grzybowski and coworkers. 26,27 Guided by the above expectation, we propose a computational framework of heuristics-aided quantum chemistry (HAQC) suitable for exploring complex and large-scale reaction mechanisms.…”

Section: Introductionmentioning

confidence: 99%

Complex Chemical Reaction Networks from Heuristics-Aided Quantum Chemistry

Rappoport

Galvin

Zubarev

et al. 2014

J. Chem. Theory Comput.

124

155

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While structures and reactivities of many small molecules can be computed efficiently and accurately using quantum chemical methods, heuristic approaches remain essential for modeling complex structures and large-scale chemical systems. Here we present heuristics-aided quantum chemical methodology applicable to complex chemical reaction networks such as those arising in metabolism and prebiotic chemistry. Chemical heuristics offer an expedient way of traversing high-dimensional reactive potential energy surfaces and are combined here with quantum chemical structure optimizations, which yield the structures and energies of the reaction intermediates and products. Application of heuristics-aided quantum chemical methodology to the formose reaction of prebiotic evolution reproduces the experimentally observed reaction products, major reaction pathways, and autocatalytic cycles.

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Section: Introductionmentioning

confidence: 99%

Complex Chemical Reaction Networks from Heuristics-Aided Quantum Chemistry

Rappoport

Galvin

Zubarev

et al. 2014

J. Chem. Theory Comput.

124

155

View full text Add to dashboard Cite

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“…Computer-aided synthesis [3,4] also had its origins in that decade. Both developments were highly funded and considered important, but neither has developed into major fields, and both are primarily historic curiosities.…”

Section: Origins Of Computational Metric and Informatics Disciplinesmentioning

confidence: 99%

A short history of chemometrics: a personal view

Brereton

2014

Journal of Chemometrics

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This article traces chemometrics back to its origins in scientific computing in the 1960s. Its development is compared in other computational disciplines such as bioinformatics. The change in geographical origins of papers published in the core chemometrics literature is discussed. It is concluded that the level of core activities in this area has hardly changed over several decades, whilst there has been a significant expansion in non-expert users of packages over this period. It is estimated that around 2% of people encountering chemometrics in their research can be considered real experts. The problems of non-experts using chemometrics methods with limited knowledge of the statistical fundamentals are explored. The contrasting development of chemometrics compared with, for example, computational chemistry and bioinformatics, is interpreted in terms of the changing financial pressures on research over its key developmental phase, as illustrated by the change in academic finance in the UK over the past 50 years.

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“…The first system for computer-aided organic synthesis (CAOS) was the one published by Corey and Wipke in 1969, namely OCSS [4], which was the predecessor of the better known LHASA [5]. In 1972, Bersohn published his synthesis design program [6], which did not interact with the user.…”

Section: Introductionmentioning

confidence: 99%

Selective Search Focusing on Retro-Synthetically Important Bonds in A Synthesis Design System

Tanaka¹,

Kawai²,

Takabatake³

et al. 2009

J. Comput. Aided Chem.

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A new capability has been added to the synthesis design system SYNSUP [1]. The new module generates synthetic routes that focus on key-bonds. Key-bonds are selected according to their spatial relationships to chiral atoms and central atoms of functional groups. When the key-bonds cannot be formed by any reaction known to SYNSUP, then structure changes in the vicinity of the bonds are effected so that the key-bonds can be disconnected in a retro-synthetic pathway. We called the fashion "selective search". Such structure changes were studied, using 27 reported total synthesis of 25 naturally occurring compounds. This kind of selective search has been shown to be useful and practical for relatively complicated molecules.

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Computer-Assisted Design of Complex Organic Syntheses

Cited by 587 publications

References 26 publications

Complex Chemical Reaction Networks from Heuristics-Aided Quantum Chemistry

Complex Chemical Reaction Networks from Heuristics-Aided Quantum Chemistry

A short history of chemometrics: a personal view

Selective Search Focusing on Retro-Synthetically Important Bonds in A Synthesis Design System

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