An improved synthesis of the [5.6.7]-tricyclic core of cyrneine B and glaucopine C
Literature Information
Publication Date
2020-08-25
DOI
10.1039/D0QO00758G
Impact Factor
5.281
Authors
Guo-Jie Wu, Xiu Han
View Original
Abstract
A new route for the synthesis of the [5.6.7]-tricyclic core structure of cyrneine B and glaucopine C is presented. The key transformations included an efficient Suzuki cross-coupling of the densely substituted cyclopentenyl triflate with cyclic vinylboronate and a highly regio- and stereoselective intramolecular deconjugative alkylation. The synthetic route allowed for the construction of the [5.6.7]-tricyclic core within a 16-step linear sequence from the commercially available 2-methylcyclopentanone, which is five steps shorter than the first generation route as reported previously by us.
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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
![Ethyl ({[(2-methyl-2-propanyl)oxy]carbonyl}amino)(2-pyridinyl)acetate structure](https://static.chemtradehub.com/structs/313/313490-90-3-dd15.webp "Ethyl ({[(2-methyl-2-propanyl)oxy]carbonyl}amino)(2-pyridinyl)acetate structure")
Ethyl ({[(2-methyl-2-propanyl)oxy]carbonyl}amino)(2-pyridinyl)acetate
CAS Number:
313490-90-3
Molecular Formula:
C14H20N2O4
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