The 30,000th item was added to cIRcle, UBC’s Digital Repository!

Title: The chemistry of thujone : the synthesis of rose oil components and germacrane analogues /

Author: Gunning, Philip James /  Degree: Doctor of Philosophy – PhD /  Program: Chemistry /  Date: 1991

Abstract: This thesis is concerned with the synthesis of natural products from thujone (1), a readily available starting material obtained from Western red cedar. The first part of this study investigates the synthesis of the commercially important fragrances, (β-damascone (8) and β-damascenone (24), which are components of rose oil. Thujone can be efficiently converted to the dimethylated thujone derivative 59 in a two step alkylation process. After the formation of the trimethylsilyl cyanohydrins, 77 and 78, the cyclopropane and isopropyl functionalities were cleaved to give the ketone 103. Further elaboration of 103 gave the key intermediates, 127 and 128. The unsaturated nitriles 128 and 127 can be converted to 8 and 24, respectively, by a reduction to the corresponding aldehydes followed by a Grignard reaction to attach the side-chain and subsequent oxidation. As a model study for the synthesis of 8 and 24 from a cyclohexanone derivative, the nitriles 127 and 128 were efficiently synthesised, in 81% overall yield, from 2,2,6-trimethylcyclohexanone. Formation of the cyanohydrins 149 and 150 was followed by consecutive ‘trans’ and ‘cis’ eliminations to give the nitrile 128. The nitrile 127 was produced from 128 by allylic bromination, followed by hydrolysis and dehydration. A conversion of thujone into the ketone 179, using bromine to effect cyclopropane ring-opening, was also studied. The second part of this study investigates the synthesis of ten-membered rings via a photo-induced oxidative cleavage of the alcohols 245 and 265. Treatment of 245 with lead tetraacetate under ultraviolet irradiation afforded, as the main isolated product, the ten-membered carbocycle 246. Treatment of 265 with iodobenzene diacetate under ultraviolet irradiation afforded, as the main isolated product, the bicyclic alcohol 297.

So far, this item has had the following activity (note: click on the Show Statistical Information link on the item page in cIRcle):

  • Top Country Views from Canada (4), United States of America (4), United Kingdom (1), and the Russian Federation (1)

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As part of the UBC Graduate & Undergraduate Student Workshop Series‘ events offered by UBC Library, the next cIRcle workshop is happening today at 3-4:30pm in Scarfe 155 (Neville Scarfe Building).

Would you like to have your academic work searched by Google Scholar or have your work archived in the UBC Library? Then come to this session to find out what cIRcle is, what it contains, how you can contribute and what permissions are required to submit your presentations, articles and reports. This session will be facilitated by Trevor Smith.

To register, please click here.

Above image courtesy of: Flickr: UBC Library’s Photostream

BC Nursing Leadership Institute: program evaluation report in cIRcle!


The first BC NLI pilot was conducted in March 2005 with 25 first-line nurse leaders. Successful evaluation outcomes resulted in 13 additional sessions between March 2006 and March 2010: three sessions annually with an average of 35-40 first-line nurse leaders in attendance.

Based upon the four major components of the BC NLI: a) a 4-day residential workshop, b) mentoring supports at practice sites, c) year-long leadership projects at practice sites, and d) an online knowledge network with a discussion forum, resources, and a facilitator or knowledge broker (KB).

What you’ll discover in this report:

  • Executive Summary
  • Key Outcomes
  • Notable Findings and Implication
  • Key Recommendations

To access and/or download this program evaluation report, click here or visit cIRcle at:

UBC Dentistry Research Day 2011 is on Tuesday, January 25th!

This day highlight[s] the research being done by several members of UBC’s ELDERS (Elders Link with Dental Education, Research and Service) Group, a multidisciplinary team which draws on expertise from many faculties.

The Faculty of Dentistry is honoured to include presentations on this pressing concern from a diverse and complementary group of full-time faculty, along with Dr. Lynn Beattie and Hamber Visiting Professor Dr. Asuman Kiyak. Beattie is professor emeritus, UBC Department of Medicine, Division of Geriatric Medicine, and Kiyak is professor and director of the Institute on Aging at the University of Washington, Seattle.

Click here for Event FAQs and Schedule of Events (PDF).  For more information, please contact Alison Kovacs at or 604 827-5220.

Curious about Dentistry research in cIRcle? Check out these examples and more:

Effect of Biotene® Oralbalance moisturizing liquid and MouthKote® oral moisturizer spray on human enamel measured by quantitative light-induced fluorescence method

Human masseter motor unit behavior

Quality assurance and dental hygiene care in British Columbia

Above excerpt text and image is courtesy of UBC Dentistry – The Faculty of Dentistry at The University of British Columbia’s website.

Webcasts of UBC presentations are available in cIRcle:

1.      “The “Funding Agency Panel: Opening up Access” recorded webcast is available online at:

2.       The “Developing the Cycling Route Planner” ( (an interactive trip bike route planner) by 2010 UBC Library Innovative Dissemination of Research Award recipient, Dr. Michael Brauer, was created because: 1) “the user community asked for this” and 2) “innovation is fun!”

3.       “Open Research Data” (  was an engaging session presented by Heather Piwowar, DataONE postdoc with Dryad and NESCent, UBC and who is also known as @researchremix if you are following us/cIRcle on Twitter!

4.       Learning about the UBC Wiki ( it went live in 2009; has received over 2,018,521 page views; and it is labeled as “Gardening the Wiki” since it is a growing open access tool used for and by the UBC community to create, store, and share, for example, course related information and other UBC resources.

5.       David Eaves, an expert in public policy, open government and open source methodologies, presented a riveting presentation ( on the importance and rise of the open government in our digital age. He also touched on how universities’ faculty and students could benefit from open government data research and opportunities as they relate to the increasing open access movement.

6.       UBC’s John Willinsky and two other distinguished OA advocates shared a lively panel discussion about scholarly rights and responsibilities. Be sure to watch the recorded webcast in cIRcle at:

7.       Last, but not least by any means, the recorded Keynote event webcast, “The Case for Open Data and eScience” ( by G. Sayeed Choudhury, John Hopkins University.

Quick Open Access Week 2010  Facts:

@ Open Access Week (OAW) 2010 – marked the 4th international OA event – held October 18-24, 2010

@ UBC Library invited its research and academic community to attend and/or participate

@ UBC & UBC Okanagan campuses hosted 23 OAW event sessions in October 2010

@ OA event sessions consisted of: discussion forums, lectures, seminars, workshops, and symposia

@ OA topics and timely issues presented and discussed from across different disciplines and from a

variety of perspectives (academic to governmental standpoints, etc.)

Global Open Access 2010 highlights:

1.       30 research institutions (such as Concordia University) adopted green OA mandates for faculty research articles in 2010

2.       77 schools considering or drafting OA policies per the SPARC Campus Open Access Policies (COAP) project

3.       5,936 peer-reviewed journals listed in the Directory of Open Access Journals (DOAJ)

4.       During an average week in 2010, 10 new OA repositories were launched and 115,000+ new items in the OA repositories global network.

5.       PubMed Central Canada was officially launched as a joint project of the National Research Council’s Canada Institute for Scientific and Technical Information, the Canadian Institutes of Health Research, and the US National Library of Medicine.

6.       Canada’s National Research Council announced the first steps toward a Canadian Virtual Health Library (CVHL) – joint project of the Canadian Health Libraries Association (CHLA) and the Canadian Institutes of Health Research (CIHR).

7.        SFU has signed to COPE (Compact for Open Access Equity), partner to the larger Public Knowledge Project (OA journal and monograph hosting) in BC.

Above image is courtesy of the Open Access Week ( website.

Unless otherwise identified, most of the sources listed above are courtesy of the SPARC Open Access Newsletter, issue #153 by Peter Suber published online on January 2, 2011.

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