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Use of Masked Quinones in Organic Synthesis: Efforts Directed Towards the Synthesis of Tropolonoid Natural Products

Citation

Koelsch, Peter Martin (1981) Use of Masked Quinones in Organic Synthesis: Efforts Directed Towards the Synthesis of Tropolonoid Natural Products. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/v5ga-5777. https://resolver.caltech.edu/CaltechTHESIS:05082018-144257927

Abstract

The application of quinone-derived substrates as building blocks for the synthesis of tropolonoid natural products is described. A preparation of the terpene β-dolabrin involving electrocyclic ring-opening of a bicyclo[4.l.0]heptenone enolate is outlined. A number of approaches to the recently characterized alkaloid imerubrine involving a highly efficient annelation procedure to form the benzazulenoid carbocyclic skeleton are also discussed.

[Chemical structure; see abstract in scanned thesis for details.]

Item Type:Thesis (Dissertation (Ph.D.))
Subject Keywords:Chemistry
Degree Grantor:California Institute of Technology
Division:Chemistry and Chemical Engineering
Major Option:Chemistry
Thesis Availability:Public (worldwide access)
Research Advisor(s):
  • Dervan, Peter B.
Thesis Committee:
  • Dervan, Peter B. (chair)
  • Evans, David A.
  • Bercaw, John E.
  • Grubbs, Robert H.
Defense Date:26 May 1981
Record Number:CaltechTHESIS:05082018-144257927
Persistent URL:https://resolver.caltech.edu/CaltechTHESIS:05082018-144257927
DOI:10.7907/v5ga-5777
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:10863
Collection:CaltechTHESIS
Deposited By: Mel Ray
Deposited On:08 May 2018 23:19
Last Modified:16 Apr 2021 22:13

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