This research proposal provides initial results that substantiate the utility of Mo-catalyzed Asymmetric Ring- Opening Cross-Metathesis (AROCM) in the synthesis of chiral pyrans and piperidines, two structural motifs present in myriad biologically important natural products. In addition, we outline our plans for extending this methodology to a variety of oxa- and aza-bridged [3.2.1] bicyclic substrates, and extending this methodology to olefin cross partners that can be readily functionalized. Currently, there are no other known methods for setting the chirality of 2,6-cis-substituted-pyrans and -piperidines through metathesis. The Mo-catalyzed AROCM to form chiral piperidines will be applied to the target oriented total synthesis of lobeline, a biologically active natural product part of a class of alkaloids isolated from the herb Lobelia inflate. ? ?

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Predoctoral Individual National Research Service Award (F31)
Project #
5F31GM073556-02
Application #
6967538
Study Section
Special Emphasis Panel (ZRG1-F05 (29))
Program Officer
Gaillard, Shawn R
Project Start
2004-09-01
Project End
2006-07-31
Budget Start
2005-09-01
Budget End
2006-07-31
Support Year
2
Fiscal Year
2005
Total Cost
$25,797
Indirect Cost
Name
Boston College
Department
Chemistry
Type
Schools of Arts and Sciences
DUNS #
045896339
City
Chestnut Hill
State
MA
Country
United States
Zip Code
02467