Asymmetric synthesis of (E)-Secobutanolides: total synthesis and structural revision of (+)-Litseakolide F and G
Literature Information
Publication Date
2023-10-25
DOI
10.1039/D3QO01523H
Impact Factor
5.281
Authors
Dong Guk Nam, Jin Won Lee, Hyun Sil Jung, Do Hyun Ryu
View Original
Abstract
Optically active (E)-β-branched Morita–Baylis–Hillman (MBH) esters were prepared through a catalytic Michael-aldol MBH reaction and Z → E isomerization, which were successfully carried out using both photochemical and thermal methods. In this study, we report the first asymmetric synthesis of the (E)-Secobutanolide series and (+)-Litseakolide F and G, using an optically enriched iodo MBH ester. These investigations led us to propose revised structures for the natural products (+)-Litseakolide F and G.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
![1-{3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinyl}-2,3-dihydroxy-1-propanone structure](https://static.chemtradehub.com/structs/122/1226872-27-0-e037.webp "1-{3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinyl}-2,3-dihydroxy-1-propanone structure")
1-{3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinyl}-2,3-dihydroxy-1-propanone
CAS Number:
1226872-27-0
Molecular Formula:
C25H26N6O4
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