Studies Toward an Enantioselective Total Synthesis of (+)-Duocarmycin A PDF Download
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Author: Philippe Gastaud
Publisher:
ISBN:
Category :
Languages : en
Pages : 172
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Author: Philippe Gastaud
Publisher:
ISBN:
Category :
Languages : en
Pages : 172
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Author: Todd M. Heidelbaugh
Publisher:
ISBN:
Category :
Languages : en
Pages : 694
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Author: Leonard Sung
Publisher:
ISBN: 9780549716709
Category :
Languages : en
Pages : 38
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Synthetic efforts toward the [3+1] quadrigemine alkaloids are described in this dissertation. Chapter 1 reviews the quadrigemine alkaloids from a historical perspective and discusses methods for the construction of their highly congested vicinal and diaryl all-carbon quaternary stereocenters. The application of these methods is featured in the presentation of the enantioselective syntheses of hodgkinsine and quadrigemine C.
Author: Beth Ann Plattner
Publisher:
ISBN:
Category :
Languages : en
Pages : 138
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Author: Matthew David Kowalski
Publisher:
ISBN:
Category :
Languages : en
Pages : 404
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Author: Theodore Mark Kamenecka
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ISBN:
Category :
Languages : en
Pages : 336
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Author: Jiyoung Chang
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ISBN:
Category : Cochleamycin A
Languages : en
Pages :
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Abstract: A synthetic approach to the tricyclic ring system of the unnatural enantiomer of cochleamycin A is described. An (E, Z, E)-1,6,8-nonatriene was prepared by coupling two building blocks synthesized from L-( - )-malic and L-( - )-ascorbic acids, respectively. A highly enantioselective synthesis of the fully functionalized AB ring system was achieved by a stereocontrolled intramolecular Diels-Alder reaction that proceeds via an endo transition state. The resulting cis-tetrahydroindane system was examined for its potential along two flexible pathways to construct the CD ring system. Formation of the ten-membered carbocycle was initially explored. Different cyclization methods including the Nozaki-Hiyama-Kishi reaction, ring-closing olefin metathesis, and the Ramberg-Backlund rearrangement were not effective. As an alternative way, ten-membered macrolactone formation was also investigated. C ring formation was achieved by the Yamaguchi macrolactonization protocol. Attempts to complete the D ring system of the target molecule involving reductive cyclization of bromo lactone with a Weinreb amide were unsuccessful. The Nozaki-Hiyama-Kishi reaction of bromo aldehyde 4.27 proved to be unreliable. In one instance, HRMS data was obtained indicating the possible formation of a very small amount of the target tetracyclic system. However, this observation could not be reproduced.
Author: Ivan V. Efremov
Publisher:
ISBN:
Category :
Languages : en
Pages : 552
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Author: Bryan Stroup
Publisher:
ISBN:
Category :
Languages : en
Pages : 146
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Author:
Publisher:
ISBN:
Category :
Languages : en
Pages :
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