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Progress towards the total synthesis of a spermine-conjugated dynemicin analog

Citation

Hoang, Bac H. (1998) Progress towards the total synthesis of a spermine-conjugated dynemicin analog. Master's thesis, California Institute of Technology. https://resolver.caltech.edu/CaltechTHESIS:08222013-144438603

Abstract

Progress towards the synthesis of the spermine-conjugated Dynemicin analog 4 is described. The synthetic route starts with the Michael addition of menthyl acetoacetate to trans-ethyl crotonate followed by a Dieckman condensation to form the cyclohexanedione 14 which, through a series of chemical reactions, is transformed into the quinone imine 6. Key features in the route include the Suzuki coupling reaction of the aryl boronic acid 11 and the enol triflate 12, thermal deprotection/internal amidation of the biaryl 19, cis addition of the (Z)-enediyne 33 to the quinoline 25, intramolecular acetylide addition to a carbonyl within the ketone 29, and an addition/elimination of the cyanophthalide to the quinone imine 6 to form the anthraquinone 36 utilizing the Kraus and Sugimoto methodology.

Item Type:Thesis (Master's thesis)
Subject Keywords:Chemistry
Degree Grantor:California Institute of Technology
Division:Chemistry and Chemical Engineering
Major Option:Chemical Engineering
Thesis Availability:Public (worldwide access)
Research Advisor(s):
  • Unknown, Unknown
Thesis Committee:
  • Unknown, Unknown
Defense Date:26 March 1998
Record Number:CaltechTHESIS:08222013-144438603
Persistent URL:https://resolver.caltech.edu/CaltechTHESIS:08222013-144438603
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:7932
Collection:CaltechTHESIS
Deposited By: Benjamin Perez
Deposited On:22 Aug 2013 22:25
Last Modified:02 Dec 2020 02:38

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