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9 results on '"Kongdech Savaspun"'

2. Total Synthesis of Natural Hyacinthacine C5 and Six Related Hyacinthacine C5 Epimers

Author

Anthony W Carroll, Kongdech Savaspun, Stephen G. Pyne, Masako Hoshino, Atsushi Kato, and Anthony C. Willis

Subjects
010405 organic chemistry, Chemistry, Stereochemistry, Organic Chemistry, Total synthesis, Stereoisomerism, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences, Structure–activity relationship, Epimer, Amine gas treating, Maltase, Mannich reaction, Isomaltase
Abstract

The total synthesis of natural (+)-hyacinthacine C5 was achieved, which allowed correction of its initially proposed structure, as well as six additional hyacinthacine C-type compounds. These compounds were readily accessible from two epimeric anti-1,2-amino alcohols. Keeping a common A-ring configuration, chemical manipulation occurred selectively on the B-ring of the hyacinthacine C-type products through methods of syn-dihydroxylation, SN2 ring-opening of a cyclic sulfate, and also employing either ( R)- or ( R, S)-α-methylallyl amine for the Petasis borono Mannich reaction. Our small analogue library was then assessed for its glycosidase inhibitory potency against a panel of glycosidases. (-)-6- Epi-hyacinthacine C5 and (+)-7- epi-hyacinthacine C5 (compound names are based on the corrected structure of hyacinthacine C5) proved most active, with inhibitory activities ranging between weak (IC50 = 130 μM) and moderate (IC50 = 9.9 μM) against the α-glucosidases of rat intestinal maltase, isomaltase, and sucrase, thus identifying potential new leads for future antidiabetic drug development.

Published
2018

4. Total Synthesis of Natural Hyacinthacine C

Author

Anthony W, Carroll, Kongdech, Savaspun, Anthony C, Willis, Masako, Hoshino, Atsushi, Kato, and Stephen G, Pyne

Subjects
Intestines, Biological Products, Structure-Activity Relationship, Dose-Response Relationship, Drug, Molecular Conformation, Animals, Stereoisomerism, alpha-Glucosidases, Pyrrolizidine Alkaloids, Rats
Abstract

The total synthesis of natural (+)-hyacinthacine C

Published
2018

5. Total Synthesis of Hyacinthacines B3, B4, and B5 and Purported Hyacinthacine B7, 7-epi-Hyacinthacine B7, and 7a-epi-Hyacinthacine B3 from a Common Precursor

Author

Kongdech Savaspun, Christopher W. G. Au, and Stephen G. Pyne

Subjects
Stereochemistry, Chemistry, Organic Chemistry, Hyacinthacine B7, Total synthesis, Organic chemistry
Abstract

The total synthesis of hyacinthacines B3, B4, and B5 and purported hyacinthacine B7, 7-epi-hyacinthacine B7, and 7a-epi-hyacinthacine B3 from a common anti-1,2-amino alcohol precursor is described. These syntheses confirmed that the proposed structures and absolute configurations of hyacinthacines B3, B4, and B5 were correct and disclosed that the proposed structure of hyacinthacine B7 was incorrect. Our synthetic and spectroscopic studies suggest that the natural hyacinthacines B5 and B7 are the same compounds; however, without access to authentic samples this cannot be unequivocally proven.

Published
2014

6. The boronic acid Mannich reaction in alkaloid synthesis

Author

Andrew S. Davis, Christopher W. G. Au, Matthew Wotherspoon, Thunwadee Ritthiwigrom, Kongdech Savaspun, and Stephen G. Pyne

Subjects
chemistry.chemical_compound, chemistry, Petasis reaction, General Chemical Engineering, Alkaloid, Pyrrolizidine, Alkaloid synthesis, Enantioselective synthesis, Organic chemistry, Indolizidine, General Chemistry, Mannich reaction, Boronic acid
Abstract

Our work on the application of the boronic acid Mannich reaction to the synthesis of pyrrolizidine alkaloids is described.

Published
2012

7. ChemInform Abstract: Total Synthesis of Hyacinthacines B3, B4, and B5and Purported Hyacinthacine B7, 7-epi-Hyacinthacine B7(V), and 7a-epi-Hyacinthacine B3(VI) from a Common Precursor

Author

Stephen G. Pyne, Kongdech Savaspun, and Christopher W. G. Au

Subjects
chemistry.chemical_compound, chemistry, Stereochemistry, Hyacinthacine B7, Total synthesis, Alcohol, General Medicine
Abstract

The title compounds are synthesized from a common anti-1,2-amino alcohol precursor The proposed structures and configurations of hyacinthacines B3 (I), B4 (II), and B5 (III) are correct.

Published
2014

8. Total synthesis of hyacinthacines B₃, B₄, and B₅ and purported hyacinthacine B₇, 7-epi-hyacinthacine B₇, and 7a-epi-hyacinthacine B₃ from a common precursor

Author

Kongdech, Savaspun, Christopher W G, Au, and Stephen G, Pyne

Subjects
Magnetic Resonance Spectroscopy, Molecular Structure, Stereoisomerism, Pyrrolizidine Alkaloids
Abstract

The total synthesis of hyacinthacines B3, B4, and B5 and purported hyacinthacine B7, 7-epi-hyacinthacine B7, and 7a-epi-hyacinthacine B3 from a common anti-1,2-amino alcohol precursor is described. These syntheses confirmed that the proposed structures and absolute configurations of hyacinthacines B3, B4, and B5 were correct and disclosed that the proposed structure of hyacinthacine B7 was incorrect. Our synthetic and spectroscopic studies suggest that the natural hyacinthacines B5 and B7 are the same compounds; however, without access to authentic samples this cannot be unequivocally proven.

Published
2014

9. ChemInform Abstract: The Boronic Acid Mannich Reaction in Alkaloid Synthesis

Author

Christopher W. G. Au, Matthew Wotherspoon, Kongdech Savaspun, Thunwadee Ritthiwigrom, Andrew S. Davis, and Stephen G. Pyne

Subjects
chemistry.chemical_compound, chemistry, Pyrrolizidine, Alkaloid synthesis, Organic chemistry, General Medicine, Mannich reaction, Boronic acid
Abstract

Our work on the application of the boronic acid Mannich reaction to the synthesis of pyrrolizidine alkaloids is described.

Published
2013

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