Chemistry 215H the HTML Project

Chemistry 215H"The HTML Project"

Winter Term, 2005

Introduction

One of the overarching goals in Chemistry 210 and 215 is for students to develop the ability to create "meaning" from new and unfamiliar "chemical information." You will recognize this most easily in the structure of your examinations and, for those of you who were in the Chem 210 SSGs, in the various assignments where you needed to use the primary literature (chemistry journals). Before 1998, the Final Examination in Chemistry 215H was crafted around giving students a list of leading questions derived from 4 or 5 unfamiliar journal articles along with copies of the articles. This was done without warning (and a little evasively) so that the students would not obsess over how to prepare for the test. After the shock of this surprising format wore off (in the first few minutes), students generally realized that this type of exam was easier than a conventional one (but only because they had studied appropriately!).

One disadvantage to this type of exam is its lack of depth. Naturally, if you are seeing the articles as well as the questions for the first time at your examination, then it is not reasonable to have questions that require a great deal of time to digest and assimilate large amounts of different information. In order to resolve this (and, not incidentally, to make an even more valuable task) you have already received the five journal articles on which your exam will be primarily based. During the term, you will be doing various tasks with respect to these articles in your SSGs. You will also have a term-long project related to these articles: you will be contributing to the construction of a mini-text related to the chemistry in these articles. This "book" will be a combination of a paper and hypertext (HTML) resource that ultimately will be available to your entire class. The various assignments related to this project are listed as "HTML" on the syllabus.

2004 SSG Journal Article Assignments

ssg 1.1-1.7: Total Synthesis of TMC-95A and -B via a New Reaction Leading to Z-Enamides. Some Preliminary Findings

on SAR – J. Am. Chem. Soc. 2004, 126, 6347-6355.

ssg 2.1-2.7: The Migrastatin Family: Discovery of Potent Cell Migration Inhibitors by Chemical Synthesis – J. Am. Chem. Soc. 2004, 126, 11326-11337.

ssg 3.1-3.7: Explorations in Organic Chemistry Leading to the Total Synthesis of Gelsemine – J. Am. Chem. Soc. 2002, 124, 9812-9824.

ssg 4.1-4.7: New Efficient Synthesis of Recorcinylic Macrolides via Ynolides: Establishment of Cycloproparadicicol

as Synthetically Feasible Preclinical Anticancer Agent Based on Hsp90 as the Target – J. Am. Chem. Soc. 2004, 126,

7881-7889.

ssg 5.1-5.7: Insights into Long-Range Structural Effects on the Stereochemistry of Aldol Condensations: A Practical

Total Synthesis of Desoxyepothilone-F – J. Am. Chem. Soc. 2001, 123, 5249-5259.

ssg 6.1-6.7: Total Synthesis and Determination of the Absolute Stereochemistry of Frondosin B – J. Am. Chem. Soc.

2001, 123, 1878-1889.

Your SSG will need to subdivide into a set of 2-3 person smaller study groups (ssg). Each ssg will be responsible for creating an analogous set of items within their Paper. Each ssg will need to have some substantial conversations about how to represent their work, how the ssg work will assemble in the SSGs contribution, and with your leaders' help, how the six SSG projects will assemble into the mini-text. The ssg jobs have been made as equitable as possible.

Each ssg will be responsible for (a) animating the mechanism of the transformation that it is assigned, this will be done for Web-access; (b) creating a visual representation for correlating the spectral data (the actual spectra whenever possible) with the product from the assigned transformation, this will be done for Web-access; and (c) answering a series of questions around which the text discussion of the chemistry will be done, this will have a print-version and an abbreviated Web-version.

Peer review of Winter 2003 & 2004 pedagogical presentation.

One of the fundamental tenets of scholarship is "building on the work of others." As you prepare to think about designing your teaching task (i.e., the HTML project!), we would like you to think about how previous SSG students elected to present their work. The goal here if for you to think about how well the explanation seems to you, how well you understand what they have done based on their work, and then what kinds of modifications you think would improve the instruction. Your goal is not to comment on the correctness of last year's chemistry, but to analyze the effectiveness of the methods selected by your peers to teach one another.

Each of you are a member of a 2-3 person ssg within your SSG section. Each of you should examine critically the features of two of the ssg sections' work from last year. Your ssg should produce commentary on the work of these other students and turn it in as an HTML document that we will archive at the Chem 215H web site. Each of the Winter, 2005 ssgs should examine the work from a Winter, 2003 and 2004 ssg section, as listed below. These can be found at the Chem 215H web site ( and listed at the Winter 2003 and 2004 HTML links.

Answer the following questions: (1) Comment on the overall structure of the framework used by the main SSG section (i.e., their main page) in terms of its design and its ease of use. (2) Comment of the structure selected by the ssg section for its presentation. (3) Comment on the effectiveness of the animation created by one of the two 2003 ssgs, and on the spectral correlation of the other. (4) Comment on the experimental section commentary used by one of the two 2004 ssgs, and on the responses to the leading questions of the other. (5) Do you get a good sense of the context of the (little) ssg group's transformation within the larger (SSG) section's reaction sequence? When you make these comments, think specifically about what was effective and what could be improved on the way these students from last year are teaching you! What sorts of things do you plan to do differently in order to make the peer-peer instruction even clearer? Finally, think about the way that this section combined their work. What other choices are there for presenting the full work of the paper?

Use examples and images you have extracted from these pages in order to support your review. You may not make links to the 2003/2004 pages. Your reports should be constructed as self-referring files in a single folder. The file structure you should use follows (using 2005 ssg 1.1 as an example, reviewing the work from ssg 1.1 from 2004 and ssg 3.2 of the 2003 project). Main folder named W05REV (review done in Winter 2005); each SSG should have a folder in there (SSG1) and each ssg a folder in this one (ssg1). There should be a two index.htm files inside (review1104.htm, i.e., sec 1.1 from 04 and review3203.htm) plus whatever other files or images are used for these reviews.

Later on in the term, as you develop your own pages, we will have a similar review process.

W 2005 comment on W 2004 and W 2003 ssgs (due date is part of HTML instruction)

(read the following table, using line 1 for instance, as "xxx ssg 1.1 from Winter 2005 will review the work of ssg 1.1 from 2004 and ssg 3.2 from 2003, and so forth)

ssg 1.1onssg 1.1 from 2004ssg 3.2 from 2003

ssg 1.2ssg 2.2ssg 4.2

ssg 1.3ssg 3.3ssg 1.6

ssg 1.4ssg 4.0ssg 5.6

ssg 1.5ssg 5.4ssg 6.2

ssg 1.6ssg 6.4ssg 3.3

ssg 1.7ssg 2.5ssg 4.3

ssg 2.1ssg 3.7ssg 5.3

ssg 2.2ssg 4.2ssg 2.4

ssg 2.3ssg 1.3ssg 3.4

ssg 2.4ssg 2.6ssg 4.4

ssg 2.5ssg 6.5ssg 6.3

ssg 2.6ssg 5.7ssg 5.3

ssg 2.7ssg 4.3ssg 2.5

ssg 3.1ssg 1.4ssg 3.5

ssg 3.2ssg 2.7ssg 4.5

ssg 3.3ssg 3.4ssg 5.6

ssg 3.4ssg 4.4ssg 2.6

ssg 3.5ssg 5.6ssg 5.5

ssg 3.6ssg 6.6ssg 2.3

ssg 3.7ssg 2.2ssg 1.1

ssg 4.0ssg 2.5ssg 3.1

ssg 4.1ssg 3.5ssg 5.6

ssg 4.2ssg 4.5ssg 3.6

ssg 4.3ssg 1.6ssg 1.2

ssg 4.4ssg 4.6ssg 6.3

ssg 4.5ssg 1.1ssg 2.5

ssg 4.6ssg 5.5ssg 4.1

ssg 4.7ssg 6.7ssg 4.5

ssg 5.1ssg 3.1ssg 1.3

ssg 5.2ssg 4.7ssg 2.3

ssg 5.3ssg 1.2ssg 3.3

ssg 5.4ssg 2.7ssg 4.3

ssg 5.5ssg 3.2ssg 1.4

ssg 5.6ssg 5.6ssg 1.6

ssg 5.7ssg 6.4ssg 2.4

ssg 6.1ssg 3.4ssg 1.4

ssg 6.2ssg 4.1ssg 5.4

ssg 6.3ssg 1.7ssg 3.6

ssg 6.4ssg 2.2ssg 4.3

ssg 6.5ssg 5.7ssg 6.6

ssg 6.6ssg 3.5ssg 1.5

ssg 6.7ssg 6.6ssg 5.5

Paper No. 1

ssg 1.1-1.7: Total Synthesis of TMC-95A and -B via a New Reaction Leading to Z-Enamides. Some Preliminary Findings on SAR – J. Am. Chem. Soc. 2004, 126, 6347-6355.

1.1 (a) mechanism for 16 to 2c; (b) spectral correlation for (E)-2c; (c) experimental section for (E)-2c; (d) find 3 papers that are related to the mechanism for one of the steps, then pick 1 paper and briefly (150-200 words, plus pictures) indicate what its conclusions are about the mechanism (also list up to 3 papers that have cited the one you have selected, with each ssg member obtaining a copy and writing a sentence about why this new author chose to cite the work); (e) provide a detailed mechanism for the conversion of (Z)-2c to (E)-2c, and state which of these isomers is the thermodynamic product (and how you know this)

1.2(a) mechanism for 27 to 3b; (b) spectral correlation for 3b; (c) experimental section for 3b; (d) find 3 papers that are related to the mechanism for one of the steps, then pick 1 paper and briefly (150-200 words, plus pictures) indicate what its conclusions are about the mechanism (also list up to 3 papers that have cited the one you have selected, with each ssg member obtaining a copy and writing a sentence about why this new author chose to cite the work); (e) explain the regioselectivity of the iodination reaction

1.3(a) mechanism for 3b to 30; (b) spectral correlation for 30 (c) experimental section for 30; (d) find 3 papers that are related to the mechanism for one of the steps, then pick 1 paper and briefly (150-200 words, plus pictures) indicate what its conclusions are about the mechanism (also list up to 3 papers that have cited the one you have selected, with each ssg member obtaining a copy and writing a sentence about why this new author chose to cite the work); (e) explain why no E/Z isomerization was observed in this Suzuki reaction (in contrast to that shown in Scheme 5 of the paper)

1.4(a) mechanism for 30 to 32; (b) spectral correlation for 32; (c) experimental section for 32; (d) find 3 papers that are related to the mechanism for one of the steps, then pick 1 paper and briefly (150-200 words, plus pictures) indicate what its conclusions are about the mechanism (also list up to 3 papers that have cited the one you have selected, with each ssg member obtaining a copy and writing a sentence about why this new author chose to cite the work); (e) explain the facial selectivity of the dihydroxylation using related examples from the literature

1.5(a) mechanism for 32 to 6b (b) spectral correlation for 6b; (c) experimental section for 6b; (d) find 3 papers that are related to the mechanism for one of the steps, then pick 1 paper and briefly (150-200 words, plus pictures) indicate what its conclusions are about the mechanism (also list up to 3 papers that have cited the one you have selected, with each ssg member obtaining a copy and writing a sentence about why this new author chose to cite the work); (e) discuss and explain the observed effects of concentration on the macrolactamization reaction (Table 3)

1.6(a) mechanism for 41a to 43a; (b) spectral correlation for 43a; (c) experimental section for 43a; (d) find 3 papers that are related to the mechanism for one of the steps, then pick 1 paper and briefly (150-200 words, plus pictures) indicate what its conclusions are about the mechanism (also list up to 3 papers that have cited the one you have selected, with each ssg member obtaining a copy and writing a sentence about why this new author chose to cite the work); (e) explain why the Jones reagent is selective for oxidation at the primary center (position 25)

1.7(a) mechanism for 43a to 1a; (b) spectral correlation for 1a; (c) experimental section for 1a; (d) find 3 papers that are related to the mechanism for one of the steps, then pick 1 paper and briefly (150-200 words, plus pictures) indicate what its conclusions are about the mechanism (also list up to 3 papers that have cited the one you have selected, with each ssg member obtaining a copy and writing a sentence about why this new author chose to cite the work); (e) explain why the authors wanted to synthesize analogues of the natural product, and compare the biological activity of the natural product and the analogues in proteasome inhibition studies.

Note: Spectral Correlation should include two things: (1) how these data support the structural assignment for the compound in question, and (2) what are the significant aspects of the spectral data that support the structural assignment relative to the compound from which it was prepared.
Paper No. 2

ssg 2.1-2.7: The Migrastatin Family: Discovery of Potent Cell Migration Inhibitors by Chemical Synthesis – J. Am. Chem. Soc. 2004, 126, 11326-11337.

2.1(a) mechanism for 18 to 19; (b) spectral correlation for 19 (c) experimental section for 19; (d) find 3 papers that are related to the mechanism for one of the steps, then pick 1 paper and briefly (150-200 words, plus pictures) indicate what its conclusions are about the mechanism (also list up to 3 papers that have cited the one you have selected, with each ssg member obtaining a copy and writing a sentence about why this new author chose to cite the work); (e) explain the diastereoselectivity of this reaction

2.2(a) mechanism for 20 to 21; (b) spectral correlation for 21; (c) experimental section for 21; (d) find 3 papers that are related to the mechanism for one of the steps, then pick 1 paper and briefly (150-200 words, plus pictures) indicate what its conclusions are about the mechanism (also list up to 3 papers that have cited the one you have selected, with each ssg member obtaining a copy and writing a sentence about why this new author chose to cite the work); (e) explain the diastereoselectivity of this reaction

2.3(a) mechanism for 27 to 29; (b) spectral correlation for 29; (c) experimental section for 29; (d) find 3 papers that are related to the mechanism for one of the steps, then pick 1 paper and briefly (150-200 words, plus pictures) indicate what its conclusions are about the mechanism (also list up to 3 papers that have cited the one you have selected, with each ssg member obtaining a copy and writing a sentence about why this new author chose to cite the work); (e) explain the diastereoselectivity of this reaction

2.4(a) mechanism for 32 to 33; (b) spectral correlation for 33; (c) experimental section for 33; (d) find 3 papers that are related to the mechanism for one of the steps, then pick 1 paper and briefly (150-200 words, plus pictures) indicate what its conclusions are about the mechanism (also list up to 3 papers that have cited the one you have selected, with each ssg member obtaining a copy and writing a sentence about why this new author chose to cite the work); (e) develop a tutorial for your classmates on the HWE reaction

2.5(a) mechanism for 33 to 34; (b) spectral correlation for 34; (c) experimental section for 34; (d) find 3 papers that are related to the mechanism for one of the steps, then pick 1 paper and briefly (150-200 words, plus pictures) indicate what its conclusions are about the mechanism (also list up to 3 papers that have cited the one you have selected, with each ssg member obtaining a copy and writing a sentence about why this new author chose to cite the work); (e) develop a tutorial for your classmates on the synthesis and applications of the Stryker reagent

2.6(a) mechanism for 34 to 35; (b) spectral correlation for 35; (c) experimental section for 35; (d) find 3 papers that are related to the mechanism for one of the steps, then pick 1 paper and briefly (150-200 words, plus pictures) indicate what its conclusions are about the mechanism (also list up to 3 papers that have cited the one you have selected, with each ssg member obtaining a copy and writing a sentence about why this new author chose to cite the work); (e) provide a detailed explanation of the challenges encountered during this acylation step, and provide a mechanism for the formation of side product 36

2.7(a) mechanism for 35 to 1; (b) spectral correlation for 1; (c) experimental section for 1; (d) find 3 papers that are related to the mechanism for one of the steps, then pick 1 paper and briefly (150-200 words, plus pictures) indicate what its conclusions are about the mechanism (also list up to 3 papers that have cited the one you have selected, with each ssg member obtaining a copy and writing a sentence about why this new author chose to cite the work); (e) discuss the biological studies of the natural product 1 and its derivatives described in this paper

Paper No. 3

ssg 3.1-3.7 Explorations in Organic Chemistry Leading to the Total Synthesis of Gelsemine – J. Am. Chem. Soc. 2002, 124, 9812-9824.

3.1(a) mechanism for 28a,b to 31; (b) spectral correlation for 31; (c) experimental section for 31; (d) find 3 papers that are related to the mechanism for one of the steps, then pick 1 paper and briefly (150-200 words, plus pictures) indicate what its conclusions are about the mechanism (also list up to 3 papers that have cited the one you have selected, with each ssg member obtaining a copy and writing a sentence about why this new author chose to cite the work); (e) provide a detailed explanation of the facial selectivity of this Claisen rearrangment