Synthesis of 5-Hydroxy-5-vinyl-2-cyclopentenones, a Family of Rare-Type Natural Products Mostly Recovered from Marine
Yoshihide Usami1, Natsuki Asada1, Chihiro Shizuma1
1Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Osaka Medical and Pharmaceutical University, 4-20-1 Nasahara, Takatsuki 569-1094, Japan.
Abstract:
The microwave-aided racemic synthesis of six 5-hydroxy-5-vinyl-2-cyclopentenone-type natural products was achieved. A key reaction involving the construction of the α-keto vinyl carbinol function was realized by applying a Mislow-Evans rearrangement of an allylic sulfoxide, which was prepared by conjugate addition of cyclopentane-1,3-dione-derived enolate to alkynyl sulfoxide to afford 5-hydroxy-3-methoxy-5-vinyl-2-cyclopentenone (1). From the common intermediate 1, five other congeneric natural products were synthesized.
Related Concept Videos
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Cycloaddition Reactions: Overview
Biosynthesis of Lipids
Five-Membered Heterocyclic Aromatic Compounds: Overview
Cycloaddition Reactions: MO Requirements for Photochemical Activation
Biosynthesis in Bacteria


![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)