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Halogenated oxabicyclo[3.2.1]octenes as building blocks for the synthesis of natural products.

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Call No.	QD400.3 .P45 2006
Author	Pelphrey, Phillip M.
Title	Halogenated oxabicyclo[3.2.1]octenes as building blocks for the synthesis of natural products.
Date	2006
Abstract	The previously synthesized 3,4-dibromo-8-oxabicyclo[3.2.1]octa-3,6-dien-2-one has been shown to be a very versatile building block for the synthesis of complex natural product structures. This key building block has been made in both enantiomerically pure forms through a tartrate mediated resolution strategy. Addition of a variety of nucleophiles across the dibromoenone moiety led to the formation of assorted β-substituted enone derivatives. Furthermore, both Suzuki and Sonogashira cross-coupling reactions were carried out with complete specificity for the β-bromine. Functionalization of the β-bromine was accomplished through various metallation protocols. The isolated double bond was found to be a highly reactive functionality contained within this molecule. Reaction with both cyclic and acyclic dienes furnished the corresponding Diels-Alder adducts. These bicyclo[5.4.0] undecanes could be functionalized further into the perhydroazulene ring system through a two-step oxidative cleavage sequence. The isolated double bond was also found to be amenable to ring-opening cross metathesis reactions with multiple olefins leading to highly functionalized tetrahydropyran derivatives. These methodologies were then combined and the synthesis of three different natural products were undertaken. The progress towards these syntheses has been discussed. Finally, there was a need to devise a large scale preparation of the title bicyclic compound which is also reported herein.
Description	1 online resource ( ix, 343 leaves) : illustrations
Format	application/pdf
Advisor	Wright, Dennis L.
Subject	Bicyclic compounds -- Reactivity. ; Natural products -- Synthesis. ; Halogens. ; Diels-Alder reaction.
College	Dartmouth College -- Department of Chemistry.
Issuing Body	Dartmouth Dissertations are made available through the Dartmouth Digital Library.
Degree	Thesis (Ph.D)--Dartmouth College.
Copyright	In Copyright. This material is protected by copyright and/or related rights. You are free to use this material in any way that is permitted by copyright law that applies to your use. For other uses, you need to obtain permission from the rights-holder(s). http://rightsstatements.org/page/InC/1.0/
DOI	https://doi.org/10.1349/ddlp.3316

Title	pelphrey2006 1
Full Text	Halogenated Oxabicyclo[3.2.1]octenes as Building Blocks for the Synthesis of Natural Products A Thesis Submitted to the Faculty in partial fulfillment of the requirements for the degree of Doctor of Philosophy in Chemistry by Phillip M. Pelphrey Dartmouth College Hanover, New Hampshire 17 May 2006

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Halogenated oxabicyclo[3.2.1]octenes as building blocks for the synthesis of natural products.

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