Stereoselective Desymmetrization Methods in the Assembly of Complex Natural Molecules

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This thesis describes the inception, design, and implementation of stereoselective desymmetrization reactions in the total synthesis of the natural products pactamycin and paspaline. In the case of pactamycin, the author develops a novel asymmetric Mannich reaction and symmetry-breaking reduction strategy to enable facile construction of the complex core architecture in fifteen steps using commercially available materials – the shortest synthesis to date. He subsequently demonstrates the flexibility of this approach in SAR investigations by highlighting the preparation of twenty-five unique pactamycin structural congeners. For paspaline, the author develops a biocatalytic desymmetrization strategy that allows the highly controlled synthesis of core stereochemistry and provides a platform for the development of new conceptual disconnections in the synthesis of "steroid-like" natural products. This thesis offers a valuable resource for students embarking on a PhD in total synthesis.

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Published on
Jun 9, 2016
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Science / Chemistry / Clinical
Science / Chemistry / Industrial & Technical
Science / Chemistry / Organic
Science / Life Sciences / Biochemistry
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Since its original appearance in 1977, Advanced Organic Chemistry has maintained its place as the premier textbook in the field, offering broad coverage of the structure, reactivity and synthesis of organic compounds. As in the earlier editions, the text contains extensive references to both the primary and review literature and provides examples of data and reactions that illustrate and document the generalizations. While the text assumes completion of an introductory course in organic chemistry, it reviews the fundamental concepts for each topic that is discussed.

The two-part fifth edition has been substantially revised and reorganized for greater clarity. Among the changes: Updated material reflecting advances in the field since 2001’s Fourth Edition, especially in computational chemistry; A companion Web site provides digital models for study of structure, reaction and selectivity; Solutions to the exercises provided to instructors online.

The material in Part A is organized on the basis of fundamental structural topics such as structure, stereochemistry, conformation and aromaticity and basic mechanistic types, including nucleophilic substitution, addition reactions, carbonyl chemistry, aromatic substitution and free radical reactions. Together with Part B: Reaction and Synthesis, the two volumes are intended to provide the advanced undergraduate or beginning graduate student in chemistry with a sufficient foundation to comprehend and use the research literature in organic chemistry.


Ultrasound scanning yields a series of sectional images. The basis for interpreting

the examination is the individual sectional image. At first

sight, it is easy to be confused by the variable appearance of an ultrasound

scan of the same region in different patients. This has numerous

causes, including differences in density, body fat, age-related differences,

overlying gas, and artifacts. In most cases the apparent discrepancies

are not based on true anatomical differences. When a systematic

scanning routine is closely followed, series of sectional images can be

obtained in every patient with remarkable consistency. Even if the

images themselves vary, the anatomical relationships that are demonstrated

remain constant.

While some excellent atlases have been published on computed tomography

and magnetic resonance imaging, it is curious that no one (to the

author’s knowledge) has taken the trouble to create a similar atlas of

sectional anatomy for abdominal ultrasound. The present atlas attempts

to fill this gap. In particular, the author hopes to provide the beginner

with a comprehensive guide to the initially confusing world of sonographic


Many have helped in the creation of this book. I wish to thank Dr. Hartwig

Schöndube and Dr. Matthias Geist, who gave me some scans. I also

thank Mrs. Stephanie Gay and Mr. Bert Sender of Bremen for their superb

rendering of the illustrations. I am also grateful to the staff at Thieme

Medical Publishers for enabling me to make this book a reality, with special

thanks to Dr. Antje Schönpflug, Mrs. Marion Holzer, and, of course,

Dr. Markus Becker.

Braunschweig, Spring 2004 Berthold Block

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