Synthesis of Vitamin K and Related Naphthoquinones via Demethoxycarbonylative Annulations and a Retro-Wittig Rearrangement
- Resource Type
- Authors
- Dipakranjan Mal; Ketaki Ghosh; Supriti Jana
- Source
- Organic Letters. 17:5800-5803
- Subject
- Acrylate
Vitamin K
Molecular Structure
Combinatorial Chemistry Techniques
Chemistry
Stereochemistry
Aryl
Organic Chemistry
Carboxylic Acids
Stereoisomerism
Vitamin k
Biochemistry
chemistry.chemical_compound
Acrylates
Cascade reaction
Wittig reaction
Molecule
Physical and Theoretical Chemistry
Naphthoquinones
- Language
- ISSN
- 1523-7052
1523-7060
Anionic annulations of 3-nucleofugal phthalides with α-alkyl(aryl)acrylates involving a demethoxycarbonylation provide a succinct synthesis of vitamin K and related naphthoquinones. Also reported is a new cascade reaction stemming from a Cope-retro-Wittig rearrangement. This cascade leads to direct formation of 1-hydroxy-4-prenyloxynaphthalene-2-carboxylates from the corresponding α-prenyl acrylate acceptors.