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

Author: Koelsch, Peter Martin

Year: 1981

Degree: Dissertation (Ph.D.)

Advisor: Dervan, Peter B.

Committee Members: Dervan, Peter B.; Evans, David A.; Bercaw, John E.; Grubbs, Robert H.

Option: Chemistry

DOI: 10.7907/v5ga-5777

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.]

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