Program from for the 38th NOS

622 Pages·2003·18.91 MB·English

Dear Colleagues:
It is with great pleasure that I welcome you to the 38th National Organic Symposium,
sponsored by the Organic Division of the American Chemical Society. This is an opportunity for
distinguished scholars, educators and research scientists to come together to present current
research, to discuss on-going projects, to disseminate information, to share knowledge and to
enjoy the camaraderie of colleagues and friends.
We are pleased to have the scenic Bloomington campus of Indiana University host this
Symposium. This Symposium will be highlighted by 14 lectures and presentations by eminent
researchers on a range of exciting topics at the forefront of organic chemistry research.
Augmenting the lectures will be nightly poster presentations featuring over 450 participants.
Considerable time will be allocated for participants to socialize with colleagues during the opening
reception on Sunday evening, informal mixers on Monday, Tuesday, and Wednesday evenings
and a Dinner-At-The-Fountain early Wednesday evening. We have made available a number of
organized and impromptu excursions to areas throughout southern Indiana - a uniquely
interesting geologic area of rolling hills, hardwood forests, limestone caves, sinkholes, and karsts.
We are also offering the opportunity to spend an afternoon visiting the Eli Lilly facilities in
Indianapolis.
Lectures and poster sessions will be centered in the stunning, newly renovated IU Auditorium
located in the center of the IU campus surrounded by the I.M. Pei designed IU Art Museum and
the world renowned Lilly Library of rare books and manuscripts.
I want to personally thank you for joining me, your friends and colleagues on the campus of
Indiana University, in the academically and culturally rich town of Bloomington, Indiana, in the
heartland of America, for the 38th National Organic Symposium where outstanding science will
combine with outstanding conversation among a group of outstanding scientists.
Sincerely,

Huw M. L. Davies
Larkin Professor of Organic Chemistry
University at Buffalo
State University of New York
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38 National Organic Symposium
Sponsors

We wish to acknowledge the kind and generous support of the many contributing
organizations.
Major Symposium Contributors include:

Lilly Research Laboratories Indiana University
Dinner-at-the-Fountain Office of the Chancellor
Wednesday, June 11, 2003 College of Arts and Sciences
Department of Chemistry
Opening Reception
Sunday, June 8, 2003

Special appreciation is extended to:

ACS Publications Aldrich Chemical Company, Inc.
Music: Dinner-at-the-Fountain Poster Session and Mixer
Poster Session and Mixer Monday, June 9, 2003
Wednesday, June 11, 2003

Bristol-Myers Squibb Co. InnoCentive, Inc.
5K Run Poster Session and Mixer
Tuesday, June 10, 2003 Tuesday, June 10, 2003

Dean of Faculties & Academic Affairs, Indiana University

Research & the University Graduate School, Indiana University

For their unrestricted sponsorship, we wish to thank:

Albany Molecular AstraZeneca
Avecia, Inc. Aventis
Celera Gilead Sciences, Inc.
Merck Research Laboratories Pfizer
Pharmacia Corporation Strem Chemicals, Inc.
Tularik Wyeth

For in-kind advertising sponsorship, we acknowledge:

Elsevier Science Organic ACS Journal
Thieme
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38 National Organic Symposium
Table of Contents: CD Version
Indiana University
Bloomington, Indiana
June 8-12, 2003
***Numbers refer to pages within the PDF document***

Schedule of Events...........................................................................5
Roger Adams Award......................................................................11
Symposium Organizers and Divisional Officers..............................12
Plenary Speakers............................................................................13
ACS Organic Division Graduate Fellows and Sponsors...................17
Lecture Abstracts
Albert Eschenmoser....................................................26
Donna G. Blackmond..................................................29
Ronald Breslow..........................................................33
Edward J. Delaney.....................................................36
David A. Evans...........................................................39
Laura L. Kiessling......................................................42
Eric T. Kool................................................................44
James L. Leighton.......................................................49
David W. C. MacMillan..............................................54
Larry E. Overman.......................................................57
Peter G. Schultz..........................................................61
Matthew D. Shair........................................................63
Timothy M. Swager.....................................................67
John L. Wood.............................................................70
Poster Abstracts
Sun., June 8, Session A................................................75
Mon., June 9, Session B............................................177
Tues., June 10, Session C..........................................337
Wed., June 11, Session D..........................................504
General Information.....................................................................606
List of Participants.......................................................................610
Index of Authors..........................................................................628
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38 National Organic Symposium
Exhibitors

We wish to acknowledge the following companies who have chosen to share
their products and information with the Symposium participants.

Exhibitor booths will be located on the mezzanine level of the IU
Auditorium.

Exhibit hours correspond with poster sessions and social mixers.

Aldrich Chemical Company, Inc.

FMC Lithium

Gilson, Inc.

John Wiley and Sons

Maybridge

Organic Publications-Royal Society of Chemistry

Strem Chemicals, Inc.

TCI America
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38 National Organic Symposium
Schedule of Events
Sunday, June 8, 2003
1:00pm - 8:00pm Registration IU Auditorium Lobby
8:00pm - 12:00am Poster Session A IU Auditorium Lobby
Opening Reception & Mezzanine
Sponsored by:
Indiana University,

Office of the Chancellor

College of Arts and Sciences

Department of Chemistry

Exhibitor booths Mezzanine

Monday, June 9, 2003
7:30am - 10:00am Registration IU Auditorium Lobby
8:30am - 9:00am Welcome & Opening IU Auditorium
Remarks: Huw Davies

MORNING SESSION Presiding: Huw Davies IU Auditorium
9:00am - 10:00am James L. Leighton
Columbia University
Strained Silacycles: A Powerful
Platform for Asymmetric and
Tandem Reaction Design

10:00am - 10:15am Discussion IU Auditorium
10:15am - 10:45am Break IU Auditorium Lobby
10:45am - 11:45am Larry E. Overman IU Auditorium
University of California, Irvine
New Methods for Enantioselective
Synthesis of Complex Polycyclic
Molecules
11:45am -12:00pm Discussion IU Auditorium
12:00pm - 1:30pm Lunch (on your own)
12:15pm - 5:30pm Activities
12:30pm - 5:30pm Tour: Eli Lilly & Co Indianapolis
Golf: Scramble Stone Crest Golf
Course
Tour: Walk in the Woods Hoosier National Forest
Tour: Limestone Quarry & Bybee Stone Co. &
Mill Independent Quarry
2:30pm - 5:30pm Workshop: Chemistry Building
Managing an Effective Job Room 033
Search
5:00pm - 7:00pm Dinner (on your own)

EVENING SESSION Presiding: Andy Evans IU Auditorium
7:00pm - 8:00pm Laura L. Kiessling
University of Wisconsin-Madison
Chemical Approaches to Controlling
Cell Surface Interactions
8:00pm - 8:15pm Discussion IU Auditorium
8:15pm - 9:15pm Peter G. Schultz IU Auditorium
The Scripps Research Institute
New Opportunities at the Interface
of Chemistry and Biology
9:15pm - 9:30pm Discussion IU Auditorium
9:30pm - 12:00am Poster Session B IU Auditorium Lobby,
Social Mixer Mezzanine & Tents
Sponsored by:
Aldrich Chemical Company
Exhibitor Booths Mezzanine
Tuesday, June 10, 2003
7:00am - 8:15am 5K Run Showalter Fountain
Sponsored by:
Bristol-Myers Squibb Co.

MORNING SESSION Presiding: Mike Martinelli IU Auditorium
8:30am - 9:30am David W. C. MacMillan
California Institute of Technology
Enantioselective Organocatalysis:
Broadly Useful Strategies for
Enantioselective Synthesis Using
Organic Catalysts
9:30am - 9:45am Discussion IU Auditorium
9:45am - 10:15am Break IU Auditorium Lobby
10:15am - 11:15am Donna G. Blackmond IU Auditorium
University of Hull
On the Origin of Asymmetric
Amplification in the Autocatalytic
Addition of Dialkylzincs to
Pyrimidyl Aldehydes
11:15am - 11:30am Discussion IU Auditorium
11:30am -12:30pm David A. Evans IU Auditorium
Harvard University
Architectural & Dynamic
Complexity in Organic Synthesis
12:30pm - 12:45pm Discussion IU Auditorium
1:00pm - 2:00pm Lunch (on your own)
1:00pm - 5:30pm Activities
Tour: Eli Lilly & Co. Indianapolis
Tour: Gypsum Mine & Co. National Gypsum Co.
Shoals, IN
2:30pm - 5:30pm Workshop: Chemistry Building
Fundamentals of Drug Room 122
Discovery
2:30pm - 5:30pm Workshop: Chemistry Building
Managing an Effective Job Room 033
Search
5:30pm - 7:30pm Dinner (on your own)
EVENING SESSION Presiding: Ed Vedejs IU Auditorium
7:30pm - 8:45pm Roger Adams Awardee
Address by: Albert
Eschenmoser
The Swiss Federal Institute of
Technology & The Scripps Research
Institute
A Sentimental Journey: From the
Biogenetic Isoprene Rule to the
Chemical Etiology of Nucleic Acid
Structure
8:45pm - 9:00pm Discussion IU Auditorium
9:00pm - 12:00am Poster Session C IU Auditorium Lobby,
Social Mixer Mezzanine & Tents
Sponsored by:
InnoCentive, Inc.
Exhibitor Booths Mezzanine
Wednesday, June 11, 2003

MORNING SESSION Presiding: Jeffrey Johnston IU Auditorium
8:30am - 9:30am Eric T. Kool
Stanford University
From Biomimetic Chemistry to
Synthetic Biology: Mimicking the
Molecules and Mechanisms of
Nature
9:30am - 9:45am Discussion IU Auditorium
9:45am - 10:15am Break IU Auditorium Lobby
10:15am - 11:15am Edward Delaney IU Auditorium
Bristol-Myers Squibb Co.
Automation and the Changing Face
of Process R&D in the
Pharmaceutical Industry
11:15am - 11:30am Discussion IU Auditorium
11:30am - 12:30pm Timothy M. Swager IU Auditorium
Massachusetts Institute of
Technology
Electronic Ploymers for Sensory
Applications
12:30pm - 12:45pm Discussion IU Auditorium
1:00pm - 2:00pm Lunch (on your own)
1:00pm - 5:30pm Activities
Tour: Eli Lilly & Co Indianapolis
Tour: Walk in the Woods Hoosier National Forest
Tour: Cave exploration Blue Springs Cavern,

Boat Trip Bedford, IN
2:30pm - 5:30pm Workshop: Chemistry Building
Funding & Grant Writing Room 033
5:30pm - 7:15pm Dinner-at-the-Fountain Tents
Sponsored by:
Lilly Research Laboratories
Music: ACS Publications

EVENING SESSION Presiding: Joe Gajewski IU Auditorium
7:30pm - 8:30pm Ronald Breslow
Columbia University
Recent Advances in Bioorganic
Chemistry
8:30pm - 8:45pm Discussion IU Auditorium
9:00pm - 12:00am Poster Session D IU Auditorium Lobby
Social Mixer & Mezzanine
Exhibitor Booths
Thursday, June 12, 2003

MORNING SESSION Presiding: Ahmed F. Abdel- IU Auditorium
9:00am - 10:00am Magid
John L. Wood
Yale University
Bridged Polycyclic Natural
Products: Inspirational Targets for
Total Synthesis
10:00am - 10:15am Discussion IU Auditorium
10:15am - 10:45am Break IU Auditorium Lobby
10:45am - 11:45am Matthew D. Shair IU Auditorium
Harvard University
Using Lessons from Nature in
Organic Synthesis
11:45am - 12:00pm Discussion IU Auditorium
12:00pm - 12:30pm Closing Remarks IU Auditorium