Diastereoselective synthesis of butenolides
10
Issued Date
2023
Copyright Date
1993
Language
eng
File Type
application/pdf
No. of Pages/File Size
v, 189 leaves : ill.
Access Rights
restricted access
Rights Holder(s)
Mahidol University
Bibliographic Citation
Thesis (Ph.D. (Organic Chemistry))--Mahidol University, 1993
Suggested Citation
Suwat Limsuvan Diastereoselective synthesis of butenolides. Thesis (Ph.D. (Organic Chemistry))--Mahidol University, 1993. Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/89657
Title
Diastereoselective synthesis of butenolides
Alternative Title(s)
การสังเคราะห์ไดแอสเตอริโอเมอร์บางชนิดของสารบิวทีโนไลด์
Author(s)
Abstract
The approaches for the construction of chiral 4-substituted butenolide and butanolide were developed by exploitation of the stereo-differentiating reactions as the following three main reaction types: 1) Enantiomer-differentiating reaction The strategy, based on kinetic controlled reaction, was purposed that one of the enantiomers of chiral epoxide could be differentiated during a Reformasky reaction with an optically active a-bromoacetate ester or reaction with an optically active enolate anion of malonate ester, leaving the other enantiomer of the epoxide, thus producing only one of the optically active adducts. 2) Double-stereodifferentaiting reaction Condensations of chiral ketone with either achiral or chiral alkynoate anion to synthesize an optically active 4-substituted butenolide were studied; the inherent diastereoface preferences of the two reactants may reinforce one another (consonant double stereodifferentiation) or oppose one another (dissonant double stereodifferentiation). 3) Diastereoface-differentiationreaction The strategy, based on collaboration of chirality of a-ketoester together with the roles of trimethylsiloxyfuran and catalyst toward diastereofacedifferentiation in the synthesis of chiral butenolide. The retrosynthesis analysis of the synthetic approach is outlined in Scheme A.
Degree Name
Doctor of Philosophy
Degree Level
Doctoral Degree
Degree Department
Faculty of Science
Degree Discipline
Organic Chemistry
Degree Grantor(s)
Mahidol University