Studies directed towards the total synthesis of (+)-sieboldine A
Name
260326846-MIT.pdf
Description
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5.52 MB
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964fd3de2a155d621b25524fd41c08bb
Author(s)
Gehling, Victor S. (Victor Scott)
Advisor(s)
Timothy F. Jamison.
Date Issued
2008
Publisher
Massachusetts Institute of Technology
Abstract
Progress towards the total synthesis of sieboldine A is described. This synthetic approach uses a nickel-catalyzed alkyne-ketone reductive cyclization to form the hydrindane core of the natural product in good yield and with excellent diastereoselectivity about the newly formed tertiary allylic alcohol ... The hydrindane product from this reductive cyclization can be transformed into the tetracyclic N,O-acetal which is two steps removed from the natural product 1. Efforts directed towards completion of the synthesis of 1 via a direct late-stage amine oxidation are presented ...
Description
Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2008.
Vita.
Includes bibliographical references.
Subjects
Chemistry.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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