OREGON STATE UNIVERSITY
The supported research will build on earlier discoveries concerning the stereospecific reagent controlled homologation (StReCH) of boronic ester derivatives by enantioenriched main group chiral carbenoids. StReCH enables a programmable iterative synthesis of stereochemically complex molecules, but to date this methodology has only been successfully demonstrated for the elaboration of polyalkylated materials. Studies designed to widen the scope of StReCH to encompass the synthesis of polyoxygenated molecules will be undertaken. In pursuing this endeavor, two types of scalemic carbenoid species capable of introducing oxygenation will be investigated: alpha-metallated oxiranes and alpha-metallated S,O-acetals. New methods for the generation of these sensitive organometallic reagents will be explored and StReCH based processes employing them will be strategically deployed for the total synthesis of representative alkaloid and polyketide natural products. With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Professor Paul R. Blakemore of the Department of Chemistry at Oregon State University. Professor Blakemore's research efforts focus on the development of new methods and concepts for the achievement of stereocontrolled organic synthesis. By targeting the development of tools that facilitate molecule building, the research will ultimately benefit society at large by speeding the discovery of biologically active agents and other potentially useful carbon based materials
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| AWARD OVERVIEW |
| Award Number |
0906409 |
Funding Agency |
National Science Foundation |
| Total Award Amount |
$426,340 |
Project Location - City |
Corvallis |
| Award Date |
08/07/2009 |
Project Location - State |
OR |
| Project Status |
More than 50% Completed |
Project Location - Zip |
97331-8571
|
| Jobs Reported |
0.46 |
Congressional District |
04 |
| Project Location - Country |
US |
|
|
Recipient Information
(Grants)
| Recipient Information (Grants) |
|
Recipient Name
|
OREGON STATE UNIVERSITY |
| Recipient DUNS Number |
053599908
|
| Recipient Address |
KERR ADMINISTRATION B306 |
| Recipient City |
CORVALLIS |
| Recipient State |
Oregon |
| Recipient Zip |
97331 |
| Recipient Congressional District |
04 |
| Recipient Country |
USA |
Required to Report Top 5
Highly Compensated Officials |
No |
Projects and Jobs Information
| Projects and Jobs Information |
| Project Title |
Oxygenated Carbenoids for Stereospecific Reagent Controlled Homologation |
| Project Status |
More than 50% Completed |
| Final Project Report Submitted |
No |
| Project Activities Description |
Chemistry |
| Quarterly Activities/Project Description |
With this NSF award, the Blakemore research group is developing a unified synthetic technique called Stereospecific Reagent Controlled Homologation ('StReCH'). The method provides a systematic and fully programmable means to prepare molecules with backbones made up of chains of carbon atoms. At the heart of the method lie a class of reactive intermediates called ‘chiral carbenoids’. These carbenoids are the fundamental building blocks of StReCH and they are joined together in any order desired by exploiting the unique chemistry of a common type of boron containing molecule called a ‘boronic ester.'
During the past quarter, research was conducted involving three different types of carbenoid reagents: 'metallated oxiranes', 'functionalized alpha-chloroalkyllithiums,' and (NEW!) 'lithiated silylmethyl triisopropylbenzoates'
Concerning 'metallated oxiranes' (MO's): work toward biologically active naturally occurring compounds of plant origin (alkaloids) using MO based StReCH continued.
Concerning 'functionalized alpha-chloroalkyllithiums': the synthesis of notional target molecules containing sequences of three asymmetrically substituted carbon atoms in a row (contiguous 'stereotriads') was successfully realized and a reproducible protocol established for the first time.
(NEW!) Concerning 'lithiated silylmethyl trisisopropylbenzoates': it was discovered that a configurationally unstable carbenoid of this nature can be used to effect an enantioselective chain-extension of a boronic ester via a putative dynamic kinetic resolution process relying on chiral ligand control. This constitutes a new type of chain-extension that we have dubbed 'stereoinductive reagent-controlled homologation' (i-StReCH). Results will be disclosed at the fall 2013 national meeting of the American Chemical Society by the senior student. |
| Jobs Created |
0.46 |
| Description of Jobs Created |
Graduate students that would otherwise be employed by the Department of Chemistry as a Graduate Teaching Assistants (GTA) often work instead as a Graduate Research Assistant (GRA) as a direct benefit of the American Recovery and Reinvestment Act (ARRA) award. GRA appointments free students from teaching obligations and allow them to focus time on conducting their laboratory based Doctor of Philosophy (PhD) research. In addition, such externally funded positions allow for the Department of Chemistry to employ other individuals as GTA's (thus, the net number of students in our graduate program has been allowed to grow as a result of the ARRA award). |
Purchaser Information
(Grants)
| Purchaser Information |
| Contracting Office ID |
Not Reported |
| Contracting Office Name |
Not Available |
| Contracting Office Region |
Not Available |
| TAS Major Program |
49-0101 |
| Award Information |
| Award Date |
08/07/2009 |
| Award Number |
0906409 |
| Order Number |
|
| Award Type |
Grants |
| Funding Agency ID |
49 |
| Funding Agency Name |
National Science Foundation |
| Funding Office Name |
Not Available |
| Awarding Agency ID |
49 |
| Awarding Agency Name |
National Science Foundation |
| Amount of Award |
$426,340 |
| Funds Invoiced/Received |
$351,864 |
| Expenditure Amount |
$355,190 |
| Infrastructure Expenditure Amount |
$0 |
| Infrastructure Purpose and Rationale |
Not Reported |
| Infrastructure Point of Contact Name |
Not Reported |
| Infrastructure Point of Contact Email |
Not Reported |
| Infrastructure Point of Contact Phone |
Not Reported |
| Infrastructure Point of Contact Address |
Not Reported |
| Infrastructure Point of Contact City |
Not Reported |
| Infrastructure Point of Contact State |
Not Reported |
| Infrastructure Point of Contact Zip |
Not Reported |
Product or Service Information
(Grants)
| Product or Service Information |
| Primary Activity Code |
U04.04 |
| Activity Description |
Chemistry |
| Sub-Awards Information |
| Sub-awards to Organizations |
0 |
| Sub-award Amounts to Organizations |
$0 |
| Sub-Awards to Individuals |
0 |
| Sub-Award Amounts to Individuals |
$0 |
| Number of Sub-awards less than $25,000/award |
0 |
| Amount of Sub-awards less than $25,000/award |
$0 |
| Number of payments to vendors greater than $25,000 |
0 |
| Total Amount of payments to vendors greater than $25,000/award |
$0 |
| Number of payments to vendors less than $25,000/award |
256 |
| Total Amount of payments to vendors less than $25,000/award |
$79,531 |
| Location Information |
| Latitude, Longitude |
44º 33' 53",
-123º 16' 44" |
| Congressional District |
04 |
| Address 1 |
Oregon State University |
| Address 2 |
|
| City |
Corvallis |
| County |
Benton |
| State |
OR |
| Zip |
97331-8571 |
|
 |