Approaches Towards the Total Synthesis of Altohyrtin A. PDF Download
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Author: Elizabeth Anne O'Connor
Publisher:
ISBN:
Category :
Languages : en
Pages :
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Author: Elizabeth Anne O'Connor
Publisher:
ISBN:
Category :
Languages : en
Pages :
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Author: Stephen Andrew Hermitage
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Category :
Languages : en
Pages :
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Author: Pierre D. Kary
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Category :
Languages : en
Pages :
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Author: Stuart Edward Bradley
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Category :
Languages : en
Pages :
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Author: Glenn C. Micalizio
Publisher:
ISBN:
Category :
Languages : en
Pages : 612
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Author: Michael F. Greaney
Publisher: Elsevier Inc. Chapters
ISBN: 012805607X
Category : Science
Languages : en
Pages : 58
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This chapter describes the synthesis of two related sesquiterpenes, anislactone A and merrilactone A. We initially accessed a tetracyclic oxetane in the merrilactone series using a Paternò–Büchi reaction but found the compound to be too underfunctionalized to advance further. We then developed an approach based on reductive epoxide ring opening, whereby a fully elaborated C-ring epoxy-cyclopentane, containing five stereocenters, could undergo reductive epoxide cleavage when treated with Ti(III). The resulting tertiary radical then participates in a 5-exo-dig cyclization onto a pendant alkyne to afford the complete carbon skeleton of both natural products. From this point, orthogonal functionalization routes enabled the synthesis of both anislactone A and merrilactone A. A second-generation merrilactone A synthesis is then described, growing out of discoveries made over the course of the first route in the area of cyclopentannulation. An iodo-aldol method was used to develop an approach to the anislactone skeleton and succeeded in producing the BC bicycle with good stereocontrol and functional group tolerance. Further functionalization, however, did not prove possible due to excessive steric hindrance around the incorporated iodo group preventing any productive transformation. This problem was solved by switching the nucleophile in the tandem-aldol process to cyanide. The resulting domino cyanide-addition aldol cyclization was then successfully employed in the formal synthesis of merrilactone A, using a late-stage [2+2] photocycloaddition to access the D-ring.
Author: Scott Adams Biller
Publisher:
ISBN:
Category : Electronic dissertations
Languages : en
Pages : 582
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Author: Michael Harmata
Publisher: Elsevier
ISBN: 008051796X
Category : Science
Languages : en
Pages : 437
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A classic in the area of organic synthesis, Strategies and Tactics in Organic Synthesis provides a forum for investigators to discuss their approach to the science and art of organic synthesis. Rather than a simple presentation of data or a second-hand analysis, we are given stories that vividly demonstrate the power of the human endeavour known as organic synthesis and the creativity and tenacity of its practitioners. First hand accounts of each project tell of the excitement of conception, the frustration of failure and the joy experienced when either rational thought and/or good fortune give rise to successful completion of a project. In this book we learn how synthesis is really done and are educated, challenged and inspired by these stories, which portray the idea that triumphs do not come without challenges. We also learn that we can meet challenges to further advance the science and art of organic synthesis, driving it forward to meet the demands of society, in discovering new reactions, creating new designs and building molecules with atom and step economies that provide solutions through function to create a better world.- Personal accounts of research in organic chemistry. - Written by internationally renowned scientists.- Details state of the art organic synthesis.
Author: Daniel E. Levy
Publisher: CRC Press
ISBN: 1420027956
Category : Medical
Languages : en
Pages : 904
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Book Description
Intrigued as much by its complex nature as by its outsider status in traditional organic chemistry, the editors of The Organic Chemistry of Sugars compile a groundbreaking resource in carbohydrate chemistry that illustrates the ease at which sugars can be manipulated in a variety of organic reactions. Each chapter contains numerous examples demonst
Author: Miguel A. Sierra
Publisher: John Wiley & Sons
ISBN: 352765464X
Category : Science
Languages : en
Pages : 297
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Book Description
Success comes in many forms and in synthesis it can be a failure that results in their ultimate successful solutions. This long-awaited sequel to "Dead Ends and Detours" retains the proven concept while featuring over 20 new case studies of failed strategies and their (successful) solutions in natural product total synthesis. Additionally, computational models are used to discuss the problem in much more detail and to provide readers with additional information not found in the primary literature. The topics range from classic synthetic reactions (e.g. Diels Alder reaction), metal-mediated coupling reactions, metathesis, and asymmetric catalysis to the importance of protecting and activating groups. This book will benefit not only graduate students in organic chemistry but also advanced researchers as they gain knowledge derived from the step-by-step analysis of mistakes made in the past and, thus be able to improve their own chemical reaction planning. With its coverage of the most commonly applied reaction types, the book perfectly complements its predecessor, which focuses on general aspects, such as reactivity and selectivity.
