INFORMATION AND GUIDELINES FOR THE SPECTROSCOPY ASSIGNMENT

FOR CHEM3004
Assignment is worth 15% of your final mark in CHEM3004
Hand-in Arrangements: Due date is 4.00pm Friday 5 June. Assignments handed in after this
date will attract significant penalties, and will be marked out of a maximum of 50% of the
total marks available for the assignment. Please hand in at the SCMB office in the usual
way. Remember to read and then sign the coversheet.
Topic: To research and understand the spectroscopic characteristics of a naturally-isolated
molecule. You can select your own compound (see p3. of this document; list has also been
placed on the 5th floor noticeboard). Your task is to write a thorough report on the structure
and structure elucidation of your compound by doing the following:
For your chosen compound:
Use SciFinder Scholar (or similar database) to find recent published information on the
spectroscopic data of the compound that you have been assigned.
First READ THE PAPER(S) CAREFULLY and show them to Prof Garson prior to the end
of week 11 to establish that you have found suitable information. There will be an opportunity
to discuss and general issues in understanding the material during one of the Thursday
workshops. Note: Prof Garson will not deal with such queries in weeks 12 or 13. In some
cases, you will find revision of the NMR data has occurred, and so you may need to read about
the original description of the NMR data and compare it with the revised data. In other
examples, the structure of the molecule has been revised, and your assignment is then to
explain why the original structure elucidation was incorrect, and how the structure was
corrected. Some papers additionally describe synthetic work on the naturally-isolated
molecule, and these are more suitable for students taking CHEM3001 alongside CHEM3004.
You will find spectroscopic data presented in a variety of styles, as follows: (a) in table form
within the main body of the article, or (b) listed within the experimental section of the article,
or (c) reproduced as actual spectra in the accompanying Supplementary Information (a
separate file to the main article).
Then, IN YOUR OWN WORDS, explain how the spectroscopic data for the selected
compound were assigned, and show how they are consistent with the structure proposed.
Describe in outline some of the techniques used in the structure elucidation, and convince me
that you understand how the structure elucidation was undertaken. If your report consists of
little more than paraphrasing content directly from the article, or there is any suggestion of
plagiarism, then you receive a low mark. It is recommended that you draft a report during
weeks 11 and 12, and that you then reread your journal article(s), and then ask yourself if your
report successfully presents your understanding of the topic.
The length of individual reports will vary, but aim for a minimum of 4-6 pages, excluding
references. Reports of 1-2 pages are likely to be too brief. Use 12 pt font, and 1.5 line spacing.

Your discussion might include (for example):

A drawing of the structure showing any stereochemical features and numbering key
centres that are mentioned in your discussion (use CHEMDRAW or similar
software);
identify unusual structural elements and explain how they were identified;
If, and how, NMR or other data is used to distinguish between alternative structures
for the compound;
Were IR, UV or MS used in the structure elucidation? In what way?
Does the molecule have elements of stereochemistry? If yes, what are they, and how
were they assigned? Points to look for include use of coupling constants, of nOe or of
NOESY or of ROESY data.
Is there any x-ray crystallographic data?
Has any absolute stereochemistry been assigned? If so, how?
A brief discussion on the use of synthetic chemistry to assist the structure elucidation
(extensive detail on steps/mechanisms etc are not needed. Feel free to reproduce
synthetic schemes directly from the manuscript by scanning or photocopying them).
A brief comment on any biological activity described in the article (do not get too
technical; remember that this is a chemistry assignment!)
For the bibliography, please use the ACS format shown in articles published in J. Org.
Chem. or J. Nat. Prod.
In particular, note that the ACS style does not include article titles or issue numbers in the
citation list. If you are using Endnote, you may need to edit the journal format used to conform
to the ACS style or edit the individual citations generated by Endnote. Citations are identified
in the document text by a superscript number.
Look carefully at the following citations that illustrate the accepted ACS style:

MARKING FORMAT: (out of 20)

Papers used relevance and information (ie. did student find and study the correct articles?):
marked out of 3 marks
Referencing of literature and formatting of bibliography to ACS style: marked out of 5 marks
Discussion and technical information (ie. content your discussion): marked out of 12 marks
(2 marks attention to spelling, grammer, writing etc; 10 marks: understanding and explanation
of technical content)
IMPORTANT: To enable Prof. Garson to check that you have not directly copied text
from the paper(s) that you read, please staple a photocopy of the key paper(s) that you
use to your assignment. Assignments submitted without providing the key paper(s) in this
way will receive zero marks.
Assignments must be submitted to TurnItIn antiplagiaism software.
Prof Mary Garson

1 May 2015

LIST OF TOPICS: no more than THREE students may sign for the same topic.
Topics excluding
synthetic chemistry
(suitable for students
taking CHEM3004 alone)

NAME

Topics that include

synthetic chemistry
(suitable for
students taking both
CHEM3001 and CHEM3004)

Nudibaccatumone

Elatenyne

Turnagainolide A

Acremolin

Varioxepine

Cochliomycin A

Conosilane

Hanishin

Simplextone C

Phomentrioloxin

Colisporifungin

Thiaplakortone

Neopetrocyclamine

Iotrochotazine

Hikiamide A

4,12-Dihydroxysterpurene

Cystargolide A

Kalihinol B

Nagilactone I

Sceptrin

Hypocoprin A

Berkelic Acid

Striatoid A

Phorbin A

Taccalonolide A

Plectosphaeroic acid

Phomapyrrolidinone

Taccabulin A

NAME