New functional group transformations can enable synthetic chemists to disconnect molecules in new ways, thereby enabling new synthesis strategies. Ideally such new technologies enable the synthesis of important molecules from untapped, perhaps more readily available, starting materials. In the right context, such methods can prove to be linchpin reactions for total synthesis and can offer new and more efficient routes to useful therapeutic agents. The proposed research will extend our fruitful studies on catalytic diboration reactions into a new range of stereoselective transformations. We will develop new strategies for constructing chiral organoboronates from simple starting materials and use these reactions to solve extant problems in synthesis.

Public Health Relevance

Single-enantiomer chiral compounds are vitally important as new materials and as medicinally relevant therapies. The proposed research will develop new technologies for the construction of such compounds from simple, readily available natural resources.

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Research Project (R01)
Project #
5R01GM059417-16
Application #
8895347
Study Section
Synthetic and Biological Chemistry B Study Section (SBCB)
Program Officer
Lees, Robert G
Project Start
1999-05-01
Project End
2018-07-31
Budget Start
2015-08-01
Budget End
2016-07-31
Support Year
16
Fiscal Year
2015
Total Cost
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
Liu, Xun; Sun, Chunrui; Mlynarski, Scott et al. (2018) Synthesis and Stereochemical Assignment of Arenolide. Org Lett 20:1898-1901
Yan, Lu; Meng, Yan; Haeffner, Fredrik et al. (2018) Carbohydrate/DBU Cocatalyzed Alkene Diboration: Mechanistic Insight Provides Enhanced Catalytic Efficiency and Substrate Scope. J Am Chem Soc 140:3663-3673
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