Synthetic Studies of 2-Acetoxyfuran and 2(3H)-Furanone as Pronucleophiles in the Asymmetric Synthesis of Butenolides

Identifier

158

Author

Stephen James Howard

Date

2010

Document Type

Dissertation

Degree Name

Doctor of Philosophy

Major

Chemistry

Concentration

Organic Chemistry

Committee Chair

Abby L Parrill

Committee Member

Theodore J Burkey

Committee Member

Tomoko Fujiwara

Committee Member

Richard L Petersen

Abstract

Enantioselective synthesis of γ-substituted butenolides is desirable due to the prevalence of these functionalities in medicinally important natural products. As organic synthons, butenolides contain four carbon atoms, each of which is capable of undergoing regioselective modification. Two complementary approaches for the construction of γ-substituted butenolides have been developed in the present work. The trapped dienolate, 2-acetoxyfuran, couples with aldehydes under mild conditions with diastereocontrol determined by the nature of catalyst, solvent, and temperature employed.An even more efficient synthesis of the butenolide architecture has been developed by the direct coupling of 2(3H)-furanone to aldehydes. Enantioselectivity is afforded by use of Takemoto's bifunctional thiourea catalysts. The simplicityand versatility of these reactions demonstrate the strong potential that the pronucleophiles 2-acetoxyfuran and 2(3H)-furanone offer for the synthesis of γ-butenolides.

Comments

Data is provided by the student.

Library Comment

Dissertation or thesis originally submitted to the local University of Memphis Electronic Theses & dissertation (ETD) Repository.

Recommended Citation

Howard, Stephen James, "Synthetic Studies of 2-Acetoxyfuran and 2(3H)-Furanone as Pronucleophiles in the Asymmetric Synthesis of Butenolides" (2010). Electronic Theses and Dissertations. 113.
https://digitalcommons.memphis.edu/etd/113